NPASS Compound

Structure

CID237901 OpenBabel06191716042D 59 67 0 0 1 0 0 0 0 0999 V2000 -3.9293 0.9347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7204 -2.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3246 -1.1506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0137 0.4055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7555 2.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8385 3.4015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8336 0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9300 0.9721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8480 -3.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3609 3.7221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5744 4.3397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8296 -4.0022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2193 2.7322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6463 3.9674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6883 0.7501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7806 -3.6932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2943 -0.7369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0864 -3.3331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8250 -0.2405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2935 -1.5459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0567 -0.1548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1628 1.0374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6313 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9476 -0.1329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3411 -1.3939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1374 -0.2654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3695 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4149 -1.0170 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2912 2.3599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9468 1.4211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -0.3357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1830 0.6222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5047 2.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4025 0.2604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3701 1.2183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9475 1.4585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2454 -2.0459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0432 -0.8888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6391 -2.2273 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7173 1.6737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2513 -0.6055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3980 0.1254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9885 -2.7150 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2454 -1.0459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1579 0.8448 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6635 -1.4145 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6742 2.4204 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1403 -0.0814 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2929 -1.0873 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.2943 -2.3549 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 5.2570 -2.6102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7149 1.6037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8445 0.3080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9307 1.0095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4034 -1.5187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0753 2.1739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2791 2.5726 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2458 -0.7100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5267 -2.6879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 27 1 0 0 0 0 4 48 1 0 0 0 0 5 56 1 0 0 0 0 6 57 1 0 0 0 0 7 58 1 0 0 0 0 8 42 1 0 0 0 0 10 11 2 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 29 2 0 0 0 0 14 33 2 0 0 0 0 15 19 1 0 0 0 0 15 30 1 0 0 0 0 16 43 1 0 0 0 0 17 20 1 0 0 0 0 18 50 1 0 0 0 0 19 49 1 0 0 0 0 20 50 1 0 0 0 0 21 31 2 0 0 0 0 21 32 1 0 0 0 0 22 34 2 0 0 0 0 22 35 1 0 0 0 0 23 42 1 0 0 0 0 24 28 1 0 0 0 0 24 45 1 0 0 0 0 25 28 1 0 0 0 0 25 49 1 0 0 0 0 26 42 1 0 0 0 0 26 49 1 0 0 0 0 27 51 2 0 0 0 0 27 59 1 0 0 0 0 28 23 1 1 0 0 0 29 30 1 0 0 0 0 29 33 1 0 0 0 0 30 36 2 0 0 0 0 31 34 1 0 0 0 0 31 44 1 0 0 0 0 32 35 2 0 0 0 0 32 45 1 0 0 0 0 33 47 1 0 0 0 0 34 48 1 0 0 0 0 35 56 1 0 0 0 0 36 45 1 0 0 0 0 36 47 1 0 0 0 0 37 43 1 6 0 0 0 37 44 1 0 0 0 0 37 50 1 0 0 0 0 38 44 1 1 0 0 0 38 46 1 0 0 0 0 38 48 1 0 0 0 0 39 43 1 6 0 0 0 39 46 1 0 0 0 0 39 59 1 0 0 0 0 40 52 2 0 0 0 0 40 57 1 0 0 0 0 41 46 1 0 0 0 0 41 53 2 0 0 0 0 41 58 1 0 0 0 0 42 54 1 1 0 0 0 43 9 1 1 0 0 0 44 17 1 6 0 0 0 45 40 1 6 0 0 0 46 55 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	810.42
Volume:	821.262
LogP:	4.049
LogD:	3.083
LogS:	-4.84
# Rotatable Bonds:	10
TPSA:	154.1
# H-Bond Aceptor:	13
# H-Bond Donor:	3
# Rings:	9
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.18
Synthetic Accessibility Score:	7.152
Fsp3:	0.587
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.631
MDCK Permeability:	1.665059789957013e-05
Pgp-inhibitor:	0.414
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.906
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.321
Plasma Protein Binding (PPB):	77.19271087646484%
Volume Distribution (VD):	1.869
Pgp-substrate:	23.29356575012207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.986
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.952
CYP2D6-substrate:	0.708
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.933

ADMET: Excretion

Clearance (CL):	2.161
Half-life (T1/2):	0.015

ADMET: Toxicity

hERG Blockers:	0.948
Human Hepatotoxicity (H-HT):	0.853
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.013
Carcinogencity:	0.106
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.945

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC237901

Natural Product ID:	NPC237901
*Common Name:**	JXLYSJRDGCGARV-XQKSVPLYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JXLYSJRDGCGARV-XQKSVPLYSA-N
Standard InCHI:	InChI=1S/C46H58N4O9/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1
SMILES:	COc1cc2N(C)[C@@H]3[C@@]4(c2cc1[C@]1(C[C@@H]2CN(CCc5c1[nH]c1c5cccc1)C[C@](C2)(O)CC)C(=O)OC)CCN1[C@H]4[C@@]([C@H]([C@]3(O)C(=O)OC)OC(=O)C)(CC)C=CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL22969
PubChem CID:	241903
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002756] Vinca alkaloids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12628396]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18778099]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	Hairy roots	n.a.	n.a.	PMID[19271765]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	Whole Plant	Tawangmangu village, Karanganyar, Central Java, Indonesia	2003-FEB	PMID[19422206]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19422206]
NPO13214	Ipomoea alba	Species	Convolvulaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22924480]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23282042]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[24773071]
NPO33310	Icacina trichantha	Species	Icacinaceae	Eukaryota	Tuber	n.a.	n.a.	PMID[25782063]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	stem-bark	Pahang, Malaysia	2003-JUN	PMID[25919190]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26285573]
NPO33310	Icacina trichantha	Species	Icacinaceae	Eukaryota	Tuber	n.a.	n.a.	PMID[26523419]
NPO17906	Anopterus macleayanus	Species	Escalloniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26600001]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26918761]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27077800]
NPO33310	Icacina trichantha	Species	Icacinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27340832]
NPO13214	Ipomoea alba	Species	Convolvulaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28006904]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28099005]
NPO8752	Xylaria cubensis	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28802670]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29319316]
NPO40720	0stoc spp. UIC 10366	Strain	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29381355]
NPO40719	0stoc spp. UIC 10279	Strain	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29381355]
NPO22780	Sphaeranthus africanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30074787]
NPO40549	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30601004]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30869890]
NPO40122	Eriolarynx iochromoides	Species	Solanaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[31070367]
NPO40132	Ficus schwarzii	Species	Moraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31935094]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32356659]
NPO40369	Tabernaemontana pachysiphon	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33112136]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6619887]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631435]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264679]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264682]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320741]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22780	Sphaeranthus africanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8752	Xylaria cubensis	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17906	Anopterus macleayanus	Species	Escalloniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13214	Ipomoea alba	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
GI50	8
IC50	129
Ki	1
Others	42

Activity Type	# Activity
Cell Line	105
CELL-LINE	6
Individual Protein	12
NON-MOLECULAR	14
Organism	1
Others	41
Protein Family	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	0.49	nM	PMID[517801]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	8.78	nM	PMID[517801]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	3.2	nM	PMID[517803]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	60.0	nM	PMID[517812]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1100.0	nM	PMID[517812]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1300.0	nM	PMID[517812]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	10.0	nM	PMID[517812]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2.0	nM	PMID[517812]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	60.0	nM	PMID[517812]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	50.0	nM	PMID[517812]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	2.0	nM	PMID[517813]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4.0	nM	PMID[517813]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6.0	nM	PMID[517813]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	1.0	nM	PMID[517813]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1.0	nM	PMID[517813]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	=	7.0	nM	PMID[517813]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3.0	nM	PMID[517816]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	6.8	nM	PMID[517818]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	6.0	nM	PMID[517818]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	5.1	nM	PMID[517818]
NPT4246	Cell Line	LS174T	Homo sapiens	IC50	=	20.0	nM	PMID[517818]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	14.0	nM	PMID[517818]
NPT2505	Cell Line	NCI-H520		IC50	=	4.5	nM	PMID[517818]
NPT2400	Cell Line	PA-1	Homo sapiens	IC50	=	4.6	nM	PMID[517818]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	6.0	nM	PMID[517819]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	6.8	nM	PMID[517819]
NPT4465	Cell Line	HCT-116/VM46	Homo sapiens	IC50	=	600.0	nM	PMID[517819]
NPT612	Individual Protein	Canalicular multispecific organic anion transporter 1	Homo sapiens	IC50	>	133000.0	nM	PMID[517820]
NPT1249	Individual Protein	Canalicular multispecific organic anion transporter 2	Homo sapiens	IC50	>	133000.0	nM	PMID[517820]
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	IC50	=	35100.0	nM	PMID[517820]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	1.8	nM	PMID[517822]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	8.8	nM	PMID[517822]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	0.5	nM	PMID[517822]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	20.2	nM	PMID[517825]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	1.5	nM	PMID[517826]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	285.0	nM	PMID[517826]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	23.0	nM	PMID[517827]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	32.0	nM	PMID[517827]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	4.4	nM	PMID[517827]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7.3	nM	PMID[517827]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	Activity	=	49.0	%	PMID[517828]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	49.0	%	PMID[517828]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	19.51	nM	PMID[517829]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7.7	nM	PMID[517830]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	500.0	nM	PMID[517831]
NPT1185	Individual Protein	Proteasome component C5	Homo sapiens	IC50	=	4280.0	nM	PMID[517832]
NPT1186	Individual Protein	Proteasome Macropain subunit	Homo sapiens	IC50	=	4900.0	nM	PMID[517832]
NPT1187	Individual Protein	Proteasome Macropain subunit MB1	Homo sapiens	IC50	=	4580.0	nM	PMID[517832]
NPT1185	Individual Protein	Proteasome component C5	Homo sapiens	IC50	>	40000.0	nM	PMID[517832]
NPT1186	Individual Protein	Proteasome Macropain subunit	Homo sapiens	IC50	=	14500.0	nM	PMID[517832]
NPT1187	Individual Protein	Proteasome Macropain subunit MB1	Homo sapiens	IC50	>	40000.0	nM	PMID[517832]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	9.4	nM	PMID[517833]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	27.0	nM	PMID[517833]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	31.0	nM	PMID[517833]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	8.1	nM	PMID[517833]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	8.7	nM	PMID[517833]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.36	nM	PMID[517834]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	IC50	=	96.0	nM	PMID[517834]
NPT4465	Cell Line	HCT-116/VM46	Homo sapiens	IC50	=	600.0	nM	PMID[517835]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	6.8	nM	PMID[517835]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	6.0	nM	PMID[517835]
NPT168	Cell Line	P388	Mus musculus	ILS	=	83.0	%	PMID[517836]
NPT381	Cell Line	OVCAR-8	Homo sapiens	IC50	=	15.0	nM	PMID[517837]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	IC50	=	200.0	nM	PMID[517837]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	900.0	nM	PMID[517838]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	2051000.0	nM	PMID[517838]
NPT1577	Cell Line	SW1573	Homo sapiens	RatioGI50	=	2388.0	n.a.	PMID[517838]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	800.0	nM	PMID[517838]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	1000.0	nM	PMID[517838]
NPT1577	Cell Line	SW1573	Homo sapiens	RatioGI50	=	1.3	n.a.	PMID[517838]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	10.0	nM	PMID[517842]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1.0	nM	PMID[517842]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	0.5	nM	PMID[517842]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	0.8	nM	PMID[517843]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	1.0	nM	PMID[517843]
NPT1577	Cell Line	SW1573	Homo sapiens	RatioGI50	=	1.0	n.a.	PMID[517843]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	0.9	nM	PMID[517843]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	2051.0	nM	PMID[517843]
NPT1577	Cell Line	SW1573	Homo sapiens	RatioGI50	=	2388.0	n.a.	PMID[517843]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	31640.0	nM	PMID[517844]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	15000.0	nM	PMID[517844]
NPT2257	Cell Line	MCF-10A	Homo sapiens	IC50	=	25860.0	nM	PMID[517844]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	0.5	nM	PMID[517845]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	=	1.0	nM	PMID[517845]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	=	70.4	nM	PMID[517845]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	6.0	nM	PMID[517846]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	6.8	nM	PMID[517846]
NPT4465	Cell Line	HCT-116/VM46	Homo sapiens	IC50	=	600.0	nM	PMID[517846]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	7.8	nM	PMID[517846]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	1410.0	nM	PMID[517847]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	11.0	nM	PMID[517848]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	11.0	nM	PMID[517848]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	12.0	nM	PMID[517848]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	14.77	nM	PMID[517850]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	54.7	nM	PMID[517850]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	5205.0	nM	PMID[517850]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	IC50	=	5846.0	nM	PMID[517850]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	21.0	nM	PMID[517852]
NPT2192	Cell Line	HEL	Homo sapiens	IC50	=	15980.0	nM	PMID[517853]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	9490.0	nM	PMID[517853]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	17740.0	nM	PMID[517853]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	37490.0	nM	PMID[517853]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	3184.0	nM	PMID[517855]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	230.0	nM	PMID[517855]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	4.6	ug.mL-1	PMID[517856]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	42.5	nM	PMID[517857]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	21.0	nM	PMID[517857]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	10.3	nM	PMID[517857]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	73.3	nM	PMID[517857]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	32.5	nM	PMID[517857]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	9.3	nM	PMID[517857]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	24.0	nM	PMID[517858]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	1.41	nM	PMID[517859]
NPT2828	Cell Line	CEM-VLB	Homo sapiens	IC50	=	392.5	nM	PMID[517859]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.82	nM	PMID[517801]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.4	nM	PMID[517803]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.7	nM	PMID[517803]
NPT27	Others	Unspecified		IC50	=	3.8	nM	PMID[517803]
NPT27	Others	Unspecified		IC50	=	4.2	nM	PMID[517803]
NPT2	Others	Unspecified		Activity	=	5.3	%	PMID[517804]
NPT2	Others	Unspecified		Activity	=	127.1	%	PMID[517804]
NPT2	Others	Unspecified		RatioGI50	>	1000.0	n.a.	PMID[517805]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.0	nM	PMID[517806]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	480.0	nM	PMID[517806]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio IC50	=	120.0	n.a.	PMID[517806]
NPT2	Others	Unspecified		Flu intensity	=	1.2	n.a.	PMID[517806]
NPT2	Others	Unspecified		Ratio	=	0.7	n.a.	PMID[517806]
NPT2	Others	Unspecified		Flu intensity	=	0.42	n.a.	PMID[517806]
NPT2	Others	Unspecified		Ratio	=	0.9	n.a.	PMID[517806]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.49	nM	PMID[517807]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8.78	nM	PMID[517807]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.82	nM	PMID[517807]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.5	nM	PMID[517809]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.0	nM	PMID[517809]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.8	nM	PMID[517809]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.6	nM	PMID[517809]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	26.0	%	PMID[517810]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	>	135000.0	nM	PMID[517815]
NPT20985	CELL-LINE	MCF7-ADR	Homo sapiens	IC50	=	10.6	nM	PMID[517816]
NPT2	Others	Unspecified		IC50	>=	110.0	nM	PMID[517818]
NPT2	Others	Unspecified		Ratio IC50	=	88.0	n.a.	PMID[517818]
NPT2	Others	Unspecified		Inhibition	=	50.0	%	PMID[517818]
NPT27	Others	Unspecified		Papp	=	38.2	ucm/s	PMID[517818]
NPT27	Others	Unspecified		Ratio	=	16.2	n.a.	PMID[517818]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	87.0	%	PMID[517818]
NPT2	Others	Unspecified		IC50	=	37.0	nM	PMID[517818]
NPT27	Others	Unspecified		Ratio	=	2.7	n.a.	PMID[517818]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	>	133000.0	nM	PMID[517820]
NPT605	Organism	Homo sapiens	Homo sapiens	DILI_severity_class	=	0.0	n.a.	PMID[517821]
NPT2	Others	Unspecified		EC50	=	48.0	nM	PMID[517824]
NPT2	Others	Unspecified		IC50	=	2059.0	nM	PMID[517825]
NPT2	Others	Unspecified		Ratio IC50	=	101.8	n.a.	PMID[517825]
NPT2	Others	Unspecified		IC50	=	2480.0	nM	PMID[517827]
NPT23298	CELL-LINE	A549/TR	Homo sapiens	IC50	=	248.27	nM	PMID[517829]
NPT23810	CELL-LINE	A2780S	Homo sapiens	IC50	=	15.73	nM	PMID[517829]
NPT23812	CELL-LINE	A2780/T	Homo sapiens	IC50	=	16890.22	nM	PMID[517829]
NPT2	Others	Unspecified		Ratio IC50	=	12.72	n.a.	PMID[517829]
NPT2	Others	Unspecified		Ratio IC50	=	1073.76	n.a.	PMID[517829]
NPT2	Others	Unspecified		IC50	=	6.7	nM	PMID[517830]
NPT2	Others	Unspecified		Ratio IC50	<	1.0	n.a.	PMID[517830]
NPT2	Others	Unspecified		IC50	=	9200.0	nM	PMID[517831]
NPT2	Others	Unspecified		Ratio IC50	=	267.0	n.a.	PMID[517834]
NPT2	Others	Unspecified		EC150	=	0.074	uM	PMID[517839]
NPT2	Others	Unspecified		Ki	=	178.0	nM	PMID[517840]
NPT2	Others	Unspecified		CC50	<	10.0	nM	PMID[517841]
NPT782	Protein Family	Tubulin	Bos taurus	OD	=	0.2	n.a.	PMID[517844]
NPT2	Others	Unspecified		IC50	=	44.0	nM	PMID[517845]
NPT2	Others	Unspecified		Ratio IC50	=	88.0	n.a.	PMID[517845]
NPT2	Others	Unspecified		Ratio IC50	=	70.4	n.a.	PMID[517845]
NPT3014	Protein Family	Tubulin	Sus scrofa	Activity	=	31.0	%	PMID[517846]
NPT2	Others	Unspecified		IC50	=	392480.0	nM	PMID[517847]
NPT2	Others	Unspecified		Ratio IC50	=	75278.3	n.a.	PMID[517847]
NPT27	Others	Unspecified		Papp	=	6.21	nm/s	PMID[517849]
NPT27	Others	Unspecified		Papp	=	130.68	nm/s	PMID[517849]
NPT27	Others	Unspecified		Ratio	=	21.05	n.a.	PMID[517849]
NPT23810	CELL-LINE	A2780S	Homo sapiens	IC50	=	22.5	nM	PMID[517850]
NPT23812	CELL-LINE	A2780/T	Homo sapiens	IC50	=	6899.0	nM	PMID[517850]
NPT2	Others	Unspecified		Ratio IC50	=	307.3	n.a.	PMID[517850]
NPT2	Others	Unspecified		Ratio IC50	=	352.4	n.a.	PMID[517850]
NPT2	Others	Unspecified		Ratio IC50	=	106.8	n.a.	PMID[517850]
NPT2	Others	Unspecified		Ratio IC50	=	278.0	n.a.	PMID[517859]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC237901 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	448
0.1-0.2	1953
0.2-0.3	7471
0.3-0.4	11752
0.4-0.5	14991
0.5-0.6	3938
0.6-0.7	1801
0.7-0.8	285
0.8-0.85	49
0.85-0.9	2
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC195788
0.9836	High Similarity	NPC260909
0.8385	Intermediate Similarity	NPC471303
0.8167	Intermediate Similarity	NPC475666
0.8127	Intermediate Similarity	NPC81939
0.8118	Intermediate Similarity	NPC329982
0.8086	Intermediate Similarity	NPC478080
0.7992	Intermediate Similarity	NPC284685
0.7969	Intermediate Similarity	NPC133609
0.7953	Intermediate Similarity	NPC469734
0.7938	Intermediate Similarity	NPC189079
0.7928	Intermediate Similarity	NPC470785
0.7909	Intermediate Similarity	NPC88923
0.7909	Intermediate Similarity	NPC100734
0.7909	Intermediate Similarity	NPC315634
0.7905	Intermediate Similarity	NPC473540
0.7888	Intermediate Similarity	NPC184680
0.7857	Intermediate Similarity	NPC470784
0.7833	Intermediate Similarity	NPC127996
0.7819	Intermediate Similarity	NPC473041
0.7782	Intermediate Similarity	NPC17437
0.7769	Intermediate Similarity	NPC473105
0.7757	Intermediate Similarity	NPC191489
0.7729	Intermediate Similarity	NPC475720
0.7729	Intermediate Similarity	NPC474192
0.7725	Intermediate Similarity	NPC477066
0.7695	Intermediate Similarity	NPC478081
0.7673	Intermediate Similarity	NPC96321
0.7638	Intermediate Similarity	NPC473187
0.7626	Intermediate Similarity	NPC478082
0.7626	Intermediate Similarity	NPC477067
0.7617	Intermediate Similarity	NPC475816
0.7592	Intermediate Similarity	NPC330009
0.7588	Intermediate Similarity	NPC475844
0.7581	Intermediate Similarity	NPC477532
0.7576	Intermediate Similarity	NPC478083
0.7556	Intermediate Similarity	NPC89549
0.7549	Intermediate Similarity	NPC475253
0.754	Intermediate Similarity	NPC174760
0.754	Intermediate Similarity	NPC477533
0.753	Intermediate Similarity	NPC303658
0.752	Intermediate Similarity	NPC148183
0.752	Intermediate Similarity	NPC152768
0.751	Intermediate Similarity	NPC131486
0.75	Intermediate Similarity	NPC244543
0.749	Intermediate Similarity	NPC473188
0.749	Intermediate Similarity	NPC21638
0.749	Intermediate Similarity	NPC169402
0.749	Intermediate Similarity	NPC469722
0.748	Intermediate Similarity	NPC477531
0.7471	Intermediate Similarity	NPC473183
0.747	Intermediate Similarity	NPC311906
0.747	Intermediate Similarity	NPC252251
0.746	Intermediate Similarity	NPC469594
0.7449	Intermediate Similarity	NPC469928
0.7442	Intermediate Similarity	NPC474183
0.7441	Intermediate Similarity	NPC209174
0.744	Intermediate Similarity	NPC198503
0.7439	Intermediate Similarity	NPC469592
0.7439	Intermediate Similarity	NPC471080
0.7431	Intermediate Similarity	NPC473185
0.743	Intermediate Similarity	NPC288110
0.7409	Intermediate Similarity	NPC116238
0.7403	Intermediate Similarity	NPC6786
0.7402	Intermediate Similarity	NPC194740
0.74	Intermediate Similarity	NPC150239
0.74	Intermediate Similarity	NPC128115
0.7398	Intermediate Similarity	NPC475778
0.7393	Intermediate Similarity	NPC277351
0.7393	Intermediate Similarity	NPC473184
0.7388	Intermediate Similarity	NPC234999
0.7362	Intermediate Similarity	NPC473458
0.7358	Intermediate Similarity	NPC87413
0.7326	Intermediate Similarity	NPC478009
0.7326	Intermediate Similarity	NPC39370
0.7326	Intermediate Similarity	NPC478010
0.732	Intermediate Similarity	NPC46561
0.732	Intermediate Similarity	NPC247803
0.7317	Intermediate Similarity	NPC471304
0.7309	Intermediate Similarity	NPC183407
0.7309	Intermediate Similarity	NPC3207
0.7295	Intermediate Similarity	NPC476106
0.7291	Intermediate Similarity	NPC222046
0.7291	Intermediate Similarity	NPC473179
0.7289	Intermediate Similarity	NPC315467
0.728	Intermediate Similarity	NPC305984
0.7276	Intermediate Similarity	NPC474688
0.7273	Intermediate Similarity	NPC162748
0.7266	Intermediate Similarity	NPC274640
0.7265	Intermediate Similarity	NPC4687
0.7258	Intermediate Similarity	NPC308137
0.7258	Intermediate Similarity	NPC310211
0.7248	Intermediate Similarity	NPC473186
0.7236	Intermediate Similarity	NPC475910
0.7233	Intermediate Similarity	NPC280799
0.7231	Intermediate Similarity	NPC214428
0.7228	Intermediate Similarity	NPC14812
0.7227	Intermediate Similarity	NPC471513
0.7226	Intermediate Similarity	NPC471979
0.7224	Intermediate Similarity	NPC277350
0.722	Intermediate Similarity	NPC323752
0.722	Intermediate Similarity	NPC323198
0.722	Intermediate Similarity	NPC473182
0.7216	Intermediate Similarity	NPC179287
0.7213	Intermediate Similarity	NPC162484
0.7206	Intermediate Similarity	NPC469743
0.7196	Intermediate Similarity	NPC478006
0.7194	Intermediate Similarity	NPC132642
0.7189	Intermediate Similarity	NPC472098
0.7183	Intermediate Similarity	NPC184408
0.7176	Intermediate Similarity	NPC82472
0.7172	Intermediate Similarity	NPC475112
0.7172	Intermediate Similarity	NPC291535
0.7172	Intermediate Similarity	NPC475085
0.7171	Intermediate Similarity	NPC74969
0.717	Intermediate Similarity	NPC477393
0.7166	Intermediate Similarity	NPC39679
0.7165	Intermediate Similarity	NPC60621
0.716	Intermediate Similarity	NPC329747
0.7154	Intermediate Similarity	NPC208084
0.7153	Intermediate Similarity	NPC45048
0.7149	Intermediate Similarity	NPC72211
0.7148	Intermediate Similarity	NPC303374
0.7143	Intermediate Similarity	NPC14288
0.7143	Intermediate Similarity	NPC474701
0.7137	Intermediate Similarity	NPC144452
0.7137	Intermediate Similarity	NPC469589
0.7131	Intermediate Similarity	NPC267423
0.7126	Intermediate Similarity	NPC472099
0.7126	Intermediate Similarity	NPC249583
0.7122	Intermediate Similarity	NPC472589
0.7121	Intermediate Similarity	NPC24370
0.7121	Intermediate Similarity	NPC319232
0.7121	Intermediate Similarity	NPC202503
0.712	Intermediate Similarity	NPC48353
0.7117	Intermediate Similarity	NPC279589
0.7117	Intermediate Similarity	NPC471978
0.7116	Intermediate Similarity	NPC477396
0.7111	Intermediate Similarity	NPC314882
0.7111	Intermediate Similarity	NPC472588
0.711	Intermediate Similarity	NPC151171
0.7107	Intermediate Similarity	NPC243834
0.7107	Intermediate Similarity	NPC70956
0.7104	Intermediate Similarity	NPC95240
0.7104	Intermediate Similarity	NPC322135
0.7102	Intermediate Similarity	NPC162730
0.7094	Intermediate Similarity	NPC477395
0.7094	Intermediate Similarity	NPC469452
0.7093	Intermediate Similarity	NPC124920
0.7093	Intermediate Similarity	NPC34580
0.7093	Intermediate Similarity	NPC118559
0.7093	Intermediate Similarity	NPC304307
0.7092	Intermediate Similarity	NPC478074
0.7092	Intermediate Similarity	NPC39500
0.7091	Intermediate Similarity	NPC132385
0.7085	Intermediate Similarity	NPC300156
0.7083	Intermediate Similarity	NPC469450
0.7082	Intermediate Similarity	NPC115588
0.708	Intermediate Similarity	NPC23294
0.7078	Intermediate Similarity	NPC306376
0.7071	Intermediate Similarity	NPC478012
0.7071	Intermediate Similarity	NPC478011
0.707	Intermediate Similarity	NPC280272
0.7068	Intermediate Similarity	NPC201697
0.7066	Intermediate Similarity	NPC100547
0.7066	Intermediate Similarity	NPC70259
0.7066	Intermediate Similarity	NPC471762
0.7061	Intermediate Similarity	NPC325976
0.7059	Intermediate Similarity	NPC13603
0.7056	Intermediate Similarity	NPC193777
0.7055	Intermediate Similarity	NPC207620
0.7054	Intermediate Similarity	NPC79107
0.7054	Intermediate Similarity	NPC475424
0.7052	Intermediate Similarity	NPC94157
0.7052	Intermediate Similarity	NPC264176
0.705	Intermediate Similarity	NPC321592
0.705	Intermediate Similarity	NPC54803
0.7046	Intermediate Similarity	NPC314176
0.7045	Intermediate Similarity	NPC301501
0.7045	Intermediate Similarity	NPC473565
0.7044	Intermediate Similarity	NPC473833
0.7043	Intermediate Similarity	NPC51388
0.7041	Intermediate Similarity	NPC329932
0.704	Intermediate Similarity	NPC303951
0.7038	Intermediate Similarity	NPC223409
0.7037	Intermediate Similarity	NPC473800
0.7034	Intermediate Similarity	NPC154922
0.7033	Intermediate Similarity	NPC474116
0.7031	Intermediate Similarity	NPC169716
0.703	Intermediate Similarity	NPC469451
0.7028	Intermediate Similarity	NPC470931
0.7027	Intermediate Similarity	NPC261251
0.7027	Intermediate Similarity	NPC478078
0.7025	Intermediate Similarity	NPC131017
0.7025	Intermediate Similarity	NPC43787
0.7025	Intermediate Similarity	NPC205934
0.7023	Intermediate Similarity	NPC284888
0.7022	Intermediate Similarity	NPC85879
0.7022	Intermediate Similarity	NPC53255
0.7016	Intermediate Similarity	NPC231924

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC237901 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	591
0.2-0.3	861
0.3-0.4	1947
0.4-0.5	2849
0.5-0.6	1999
0.6-0.7	606
0.7-0.8	49
0.8-0.85	0
0.85-0.9	0
0.9-0.95	4
0.95-1	10

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8465	Approved
1.0	High Similarity	NPD8467	Approved
1.0	High Similarity	NPD8466	Approved
0.9836	High Similarity	NPD8460	Approved
0.9836	High Similarity	NPD8459	Approved
0.9595	High Similarity	NPD8426	Approved
0.9595	High Similarity	NPD8425	Approved
0.9592	High Similarity	NPD8429	Approved
0.9592	High Similarity	NPD8428	Approved
0.9592	High Similarity	NPD8427	Approved
0.9587	High Similarity	NPD8364	Approved
0.9587	High Similarity	NPD8363	Approved
0.9508	High Similarity	NPD8365	Clinical (unspecified phase)
0.9412	High Similarity	NPD8489	Phase 1
0.7992	Intermediate Similarity	NPD7956	Approved
0.7992	Intermediate Similarity	NPD7955	Approved
0.7909	Intermediate Similarity	NPD7803	Approved
0.7782	Intermediate Similarity	NPD8358	Approved
0.7757	Intermediate Similarity	NPD7708	Approved
0.7557	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5632	Approved
0.7295	Intermediate Similarity	NPD3003	Approved
0.7291	Intermediate Similarity	NPD7194	Discontinued
0.7289	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4373	Phase 2
0.7287	Intermediate Similarity	NPD7558	Phase 2
0.7273	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD5903	Approved
0.7269	Intermediate Similarity	NPD5902	Approved
0.7248	Intermediate Similarity	NPD4885	Approved
0.7248	Intermediate Similarity	NPD7796	Approved
0.7248	Intermediate Similarity	NPD7797	Approved
0.7214	Intermediate Similarity	NPD7181	Phase 3
0.7208	Intermediate Similarity	NPD5488	Discontinued
0.7205	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4952	Phase 3
0.7166	Intermediate Similarity	NPD5658	Approved
0.7159	Intermediate Similarity	NPD8091	Phase 3
0.7127	Intermediate Similarity	NPD5482	Discontinued
0.7115	Intermediate Similarity	NPD6985	Discontinued
0.7083	Intermediate Similarity	NPD8016	Phase 3
0.7083	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7859	Phase 2
0.7055	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1768	Approved
0.7041	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5003	Discontinued
0.703	Intermediate Similarity	NPD6517	Phase 3
0.703	Intermediate Similarity	NPD6716	Phase 1
0.7023	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6962	Phase 2
0.6996	Remote Similarity	NPD4897	Phase 2
0.6996	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7426	Phase 1
0.6985	Remote Similarity	NPD8463	Approved
0.6984	Remote Similarity	NPD7069	Discontinued
0.6982	Remote Similarity	NPD6531	Approved
0.6982	Remote Similarity	NPD6530	Approved
0.698	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD5506	Approved
0.6965	Remote Similarity	NPD5507	Approved
0.6953	Remote Similarity	NPD7925	Phase 2
0.6953	Remote Similarity	NPD7924	Phase 2
0.6952	Remote Similarity	NPD8359	Phase 2
0.6951	Remote Similarity	NPD4601	Approved
0.6951	Remote Similarity	NPD4600	Approved
0.6934	Remote Similarity	NPD8255	Phase 2
0.6929	Remote Similarity	NPD6790	Phase 1
0.6928	Remote Similarity	NPD8524	Approved
0.692	Remote Similarity	NPD5429	Discontinued
0.692	Remote Similarity	NPD7222	Phase 2
0.6908	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6456	Discontinued
0.6902	Remote Similarity	NPD5612	Discontinued
0.6897	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2916	Discontinued
0.6882	Remote Similarity	NPD5450	Discontinued
0.6877	Remote Similarity	NPD7470	Discontinued
0.6875	Remote Similarity	NPD3986	Discontinued
0.6875	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7417	Discontinued
0.6857	Remote Similarity	NPD5512	Phase 3
0.6853	Remote Similarity	NPD1392	Approved
0.6848	Remote Similarity	NPD7395	Discontinued
0.6846	Remote Similarity	NPD7548	Discontinued
0.6842	Remote Similarity	NPD7853	Phase 2
0.6838	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8421	Discontinued
0.6832	Remote Similarity	NPD7994	Phase 2
0.683	Remote Similarity	NPD6494	Phase 2
0.6811	Remote Similarity	NPD5416	Discontinued
0.679	Remote Similarity	NPD2564	Approved
0.679	Remote Similarity	NPD4499	Approved
0.679	Remote Similarity	NPD2565	Phase 2
0.6779	Remote Similarity	NPD3006	Discontinued
0.6758	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7688	Phase 1
0.6755	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8403	Phase 1
0.6746	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD6220	Phase 3
0.6742	Remote Similarity	NPD6964	Approved
0.6742	Remote Similarity	NPD6963	Approved
0.6742	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6242	Discontinued
0.6719	Remote Similarity	NPD7452	Approved
0.6719	Remote Similarity	NPD7453	Approved
0.6718	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD5479	Discontinued
0.6715	Remote Similarity	NPD8442	Discontinued
0.6715	Remote Similarity	NPD8102	Discontinued
0.6712	Remote Similarity	NPD8525	Approved
0.6706	Remote Similarity	NPD8098	Approved
0.6705	Remote Similarity	NPD3259	Approved
0.6705	Remote Similarity	NPD4328	Approved
0.6692	Remote Similarity	NPD3925	Approved
0.6691	Remote Similarity	NPD8244	Phase 2
0.6691	Remote Similarity	NPD8101	Phase 3
0.668	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.668	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4418	Discontinued
0.6679	Remote Similarity	NPD7781	Approved
0.6679	Remote Similarity	NPD5559	Phase 2
0.6679	Remote Similarity	NPD6228	Discontinued
0.6679	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6679	Remote Similarity	NPD7780	Approved
0.6667	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6656	Remote Similarity	NPD8357	Approved
0.6654	Remote Similarity	NPD8096	Phase 3
0.6654	Remote Similarity	NPD5022	Discontinued
0.6654	Remote Similarity	NPD8097	Phase 3
0.6643	Remote Similarity	NPD8284	Discontinued
0.6642	Remote Similarity	NPD7952	Approved
0.6642	Remote Similarity	NPD7953	Approved
0.6642	Remote Similarity	NPD7789	Approved
0.6642	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7951	Approved
0.6642	Remote Similarity	NPD7790	Approved
0.6642	Remote Similarity	NPD7791	Approved
0.6642	Remote Similarity	NPD7950	Approved
0.6641	Remote Similarity	NPD8160	Phase 2
0.664	Remote Similarity	NPD8283	Approved
0.664	Remote Similarity	NPD8282	Approved
0.664	Remote Similarity	NPD56	Approved
0.663	Remote Similarity	NPD6244	Phase 3
0.663	Remote Similarity	NPD7769	Phase 3
0.663	Remote Similarity	NPD6243	Phase 3
0.6629	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8423	Phase 2
0.6627	Remote Similarity	NPD8399	Phase 1
0.6617	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD6995	Phase 1
0.6615	Remote Similarity	NPD5067	Phase 2
0.6615	Remote Similarity	NPD4502	Phase 2
0.6615	Remote Similarity	NPD5164	Discontinued
0.6615	Remote Similarity	NPD5066	Phase 2
0.6614	Remote Similarity	NPD7957	Phase 1
0.6614	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD4500	Approved
0.6614	Remote Similarity	NPD5530	Phase 1
0.6614	Remote Similarity	NPD4501	Approved
0.6604	Remote Similarity	NPD7674	Phase 3
0.6604	Remote Similarity	NPD7603	Discontinued
0.6604	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7675	Phase 3
0.6602	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4454	Phase 2
0.6592	Remote Similarity	NPD6199	Discontinued
0.6591	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6586	Remote Similarity	NPD6550	Discontinued
0.6582	Remote Similarity	NPD8468	Phase 2
0.6582	Remote Similarity	NPD8100	Phase 3
0.6575	Remote Similarity	NPD5901	Discontinued
0.6574	Remote Similarity	NPD6248	Phase 2
0.6574	Remote Similarity	NPD6249	Phase 2
0.6569	Remote Similarity	NPD4946	Phase 2
0.6565	Remote Similarity	NPD6770	Approved
0.6562	Remote Similarity	NPD2509	Approved
0.6562	Remote Similarity	NPD2510	Approved
0.6559	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5913	Phase 3
0.6553	Remote Similarity	NPD7219	Approved
0.6553	Remote Similarity	NPD7221	Approved
0.6549	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6230	Discontinued
0.6545	Remote Similarity	NPD7921	Approved
0.654	Remote Similarity	NPD5930	Phase 3
0.6538	Remote Similarity	NPD5293	Phase 2
0.6535	Remote Similarity	NPD2920	Discontinued
0.6534	Remote Similarity	NPD7946	Pre-registration
0.653	Remote Similarity	NPD8512	Phase 3
0.653	Remote Similarity	NPD7824	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data