NPASS Compound

Structure

CID299654 OpenBabel06191716102D 29 33 0 0 1 0 0 0 0 0999 V2000 -0.1698 2.5094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0126 -1.7743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1243 -0.0423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0670 1.3713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7178 2.0487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2583 -2.5423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3922 -2.0423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8564 -1.0423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2583 0.4577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9903 -0.5423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3922 0.9577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9903 -2.5423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4248 -0.8513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1286 0.7085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5126 -0.9083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7627 1.0498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1243 -2.0423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8564 -2.0423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2583 -0.5423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3922 -1.0423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0126 -0.0423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4248 0.7667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1243 -1.0423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4738 0.4577 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4738 -0.5423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5126 -0.9083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7224 -2.5423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0126 -0.0423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 15 1 0 0 0 0 4 24 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 16 2 0 0 0 0 14 28 1 0 0 0 0 15 26 2 0 0 0 0 15 29 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 6 0 0 0 18 27 1 1 0 0 0 19 20 1 0 0 0 0 19 23 1 1 0 0 0 20 25 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 24 1 6 0 0 0 23 3 1 1 0 0 0 24 25 1 1 0 0 0 25 13 1 1 0 0 0 25 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.26
Volume:	425.425
LogP:	4.607
LogD:	4.015
LogS:	-4.85
# Rotatable Bonds:	3
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.679
Synthetic Accessibility Score:	5.695
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.941
MDCK Permeability:	1.4869016013108194e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.602
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.501
30% Bioavailability (F30%):	0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.22
Plasma Protein Binding (PPB):	72.48350524902344%
Volume Distribution (VD):	1.875
Pgp-substrate:	23.45381736755371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.195
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.754
CYP3A4-substrate:	0.739

ADMET: Excretion

Clearance (CL):	5.709
Half-life (T1/2):	0.381

ADMET: Toxicity

hERG Blockers:	0.767
Human Hepatotoxicity (H-HT):	0.843
Drug-inuced Liver Injury (DILI):	0.873
AMES Toxicity:	0.125
Rat Oral Acute Toxicity:	0.719
Maximum Recommended Daily Dose:	0.846
Skin Sensitization:	0.958
Carcinogencity:	0.932
Eye Corrosion:	0.055
Eye Irritation:	0.132
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC299654

Natural Product ID:	NPC299654
*Common Name:**	HEVBJYCZSNXYKU-FUVMXNIJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HEVBJYCZSNXYKU-FUVMXNIJSA-N
Standard InCHI:	InChI=1S/C25H36O4/c1-5-16-14-28-25-13-21(29-15(2)26)22(16)24(25,4)11-9-19-20(25)7-6-17-12-18(27)8-10-23(17,19)3/h5,14,17-22,27H,1,6-13H2,2-4H3/t17-,18+,19+,20-,21+,22+,23+,24-,25+/m1/s1
SMILES:	C=CC1=CO[C@@]23[C@]([C@@H]1[C@@H](OC(=O)C)C2)(C)CC[C@H]1[C@H]3CC[C@H]2[C@]1(C)CC[C@@H](C2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431149
PubChem CID:	72702444
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001691] Steroid esters

*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
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)99818-1]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346940]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421725]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165135]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15635246]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730237]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17504571]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21185919]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	twigs and leaves	Yunnan Province, China	2008-OCT	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21954912]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22708620]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	venom	n.a.	n.a.	PMID[24050254]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28256122]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223924]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12952	Cabucala madagascariensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10043	Phebalium ozothamnoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5177	Lecanora conizaeoides	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6887	Lytanthus salicinus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12735	Halimeda macroloba	Species	Halimedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9398	Cortinarius rubellus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2498	Kochia trichophylla	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21463	Aruncus dioicus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6011	Pleurotus citrinopileatus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7884	Centaurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11515	Streptomyces plumbeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26231	Vicia villosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2917	Artemisia oranensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7543	Haplopappus venetus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12250	Strychnos fendleri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4797	Gavia immer	Species	Gaviidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10672	Vitex megapotamica	Species	Lamiaceae	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
IC50	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[457238]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	64800.0	nM	PMID[457238]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[457238]

☑ 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 NPC299654 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	186
0.1-0.2	1459
0.2-0.3	5235
0.3-0.4	15276
0.4-0.5	8192
0.5-0.6	5473
0.6-0.7	5594
0.7-0.8	1245
0.8-0.85	35
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.89	High Similarity	NPC75389
0.88	High Similarity	NPC275060
0.8641	High Similarity	NPC44537
0.8495	Intermediate Similarity	NPC74258
0.8421	Intermediate Similarity	NPC26046
0.8416	Intermediate Similarity	NPC295843
0.84	Intermediate Similarity	NPC171014
0.8387	Intermediate Similarity	NPC160304
0.8381	Intermediate Similarity	NPC241977
0.8351	Intermediate Similarity	NPC304899
0.8351	Intermediate Similarity	NPC253115
0.8333	Intermediate Similarity	NPC43063
0.8333	Intermediate Similarity	NPC79298
0.8333	Intermediate Similarity	NPC3359
0.8318	Intermediate Similarity	NPC157380
0.8318	Intermediate Similarity	NPC185287
0.8315	Intermediate Similarity	NPC206735
0.8269	Intermediate Similarity	NPC12795
0.8252	Intermediate Similarity	NPC304276
0.8252	Intermediate Similarity	NPC137462
0.8242	Intermediate Similarity	NPC5280
0.8241	Intermediate Similarity	NPC16701
0.8211	Intermediate Similarity	NPC10274
0.8211	Intermediate Similarity	NPC123252
0.8211	Intermediate Similarity	NPC219937
0.8211	Intermediate Similarity	NPC194485
0.8211	Intermediate Similarity	NPC53890
0.8208	Intermediate Similarity	NPC171126
0.8172	Intermediate Similarity	NPC474970
0.8172	Intermediate Similarity	NPC168231
0.8165	Intermediate Similarity	NPC278681
0.8165	Intermediate Similarity	NPC213761
0.8165	Intermediate Similarity	NPC35171
0.8163	Intermediate Similarity	NPC471903
0.8152	Intermediate Similarity	NPC299963
0.8125	Intermediate Similarity	NPC130840
0.8125	Intermediate Similarity	NPC219516
0.81	Intermediate Similarity	NPC208358
0.8095	Intermediate Similarity	NPC103491
0.8091	Intermediate Similarity	NPC112936
0.8065	Intermediate Similarity	NPC164424
0.8061	Intermediate Similarity	NPC205173
0.8058	Intermediate Similarity	NPC220217
0.8058	Intermediate Similarity	NPC119855
0.8043	Intermediate Similarity	NPC232023
0.8022	Intermediate Similarity	NPC157655
0.802	Intermediate Similarity	NPC155974
0.7941	Intermediate Similarity	NPC31085
0.7941	Intermediate Similarity	NPC177701
0.7935	Intermediate Similarity	NPC472504
0.7925	Intermediate Similarity	NPC16270
0.7921	Intermediate Similarity	NPC108371
0.7917	Intermediate Similarity	NPC473647
0.7912	Intermediate Similarity	NPC78545
0.7912	Intermediate Similarity	NPC304194
0.7912	Intermediate Similarity	NPC71535
0.79	Intermediate Similarity	NPC475032
0.79	Intermediate Similarity	NPC475033
0.7895	Intermediate Similarity	NPC33768
0.7895	Intermediate Similarity	NPC264005
0.7895	Intermediate Similarity	NPC269360
0.7889	Intermediate Similarity	NPC42853
0.7879	Intermediate Similarity	NPC241047
0.787	Intermediate Similarity	NPC154815
0.7864	Intermediate Similarity	NPC471467
0.7857	Intermediate Similarity	NPC287118
0.7857	Intermediate Similarity	NPC473678
0.7857	Intermediate Similarity	NPC471902
0.7857	Intermediate Similarity	NPC473690
0.7857	Intermediate Similarity	NPC312481
0.785	Intermediate Similarity	NPC183603
0.7843	Intermediate Similarity	NPC144486
0.7822	Intermediate Similarity	NPC470068
0.7812	Intermediate Similarity	NPC4309
0.7802	Intermediate Similarity	NPC5604
0.7802	Intermediate Similarity	NPC305835
0.7802	Intermediate Similarity	NPC49599
0.7802	Intermediate Similarity	NPC49627
0.78	Intermediate Similarity	NPC111834
0.78	Intermediate Similarity	NPC306797
0.78	Intermediate Similarity	NPC169270
0.78	Intermediate Similarity	NPC292718
0.7789	Intermediate Similarity	NPC6605
0.7789	Intermediate Similarity	NPC2783
0.7789	Intermediate Similarity	NPC24277
0.7789	Intermediate Similarity	NPC12774
0.7789	Intermediate Similarity	NPC121981
0.7789	Intermediate Similarity	NPC201273
0.7788	Intermediate Similarity	NPC165969
0.7778	Intermediate Similarity	NPC39453
0.7778	Intermediate Similarity	NPC247760
0.7768	Intermediate Similarity	NPC41123
0.7768	Intermediate Similarity	NPC257610
0.7768	Intermediate Similarity	NPC114939
0.7768	Intermediate Similarity	NPC145074
0.7766	Intermediate Similarity	NPC127606
0.7766	Intermediate Similarity	NPC475798
0.7766	Intermediate Similarity	NPC255882
0.7766	Intermediate Similarity	NPC256567
0.7755	Intermediate Similarity	NPC160506
0.7755	Intermediate Similarity	NPC475416
0.7755	Intermediate Similarity	NPC120539
0.7755	Intermediate Similarity	NPC471901
0.7753	Intermediate Similarity	NPC3403
0.7745	Intermediate Similarity	NPC317019
0.7745	Intermediate Similarity	NPC473510
0.7742	Intermediate Similarity	NPC5985
0.7732	Intermediate Similarity	NPC57954
0.7732	Intermediate Similarity	NPC213832
0.7723	Intermediate Similarity	NPC210337
0.7723	Intermediate Similarity	NPC274793
0.7723	Intermediate Similarity	NPC471770
0.7723	Intermediate Similarity	NPC253586
0.7723	Intermediate Similarity	NPC473555
0.7723	Intermediate Similarity	NPC278939
0.7719	Intermediate Similarity	NPC6193
0.7717	Intermediate Similarity	NPC236237
0.7717	Intermediate Similarity	NPC102253
0.7717	Intermediate Similarity	NPC322313
0.7714	Intermediate Similarity	NPC278628
0.7714	Intermediate Similarity	NPC231530
0.7708	Intermediate Similarity	NPC134197
0.7706	Intermediate Similarity	NPC73050
0.77	Intermediate Similarity	NPC210214
0.77	Intermediate Similarity	NPC279974
0.7692	Intermediate Similarity	NPC477817
0.7692	Intermediate Similarity	NPC196471
0.7692	Intermediate Similarity	NPC472501
0.7692	Intermediate Similarity	NPC471045
0.7692	Intermediate Similarity	NPC301707
0.7692	Intermediate Similarity	NPC10232
0.7692	Intermediate Similarity	NPC477819
0.7692	Intermediate Similarity	NPC297617
0.7692	Intermediate Similarity	NPC160583
0.7692	Intermediate Similarity	NPC187302
0.7692	Intermediate Similarity	NPC97487
0.7692	Intermediate Similarity	NPC189588
0.7684	Intermediate Similarity	NPC294438
0.7684	Intermediate Similarity	NPC264317
0.7684	Intermediate Similarity	NPC474189
0.7684	Intermediate Similarity	NPC474349
0.7677	Intermediate Similarity	NPC470375
0.7677	Intermediate Similarity	NPC246860
0.7677	Intermediate Similarity	NPC470376
0.767	Intermediate Similarity	NPC222875
0.767	Intermediate Similarity	NPC268829
0.767	Intermediate Similarity	NPC25177
0.767	Intermediate Similarity	NPC474022
0.767	Intermediate Similarity	NPC247701
0.767	Intermediate Similarity	NPC470054
0.767	Intermediate Similarity	NPC49532
0.767	Intermediate Similarity	NPC295110
0.7667	Intermediate Similarity	NPC14112
0.7667	Intermediate Similarity	NPC93662
0.7667	Intermediate Similarity	NPC278091
0.7667	Intermediate Similarity	NPC78067
0.7667	Intermediate Similarity	NPC86305
0.766	Intermediate Similarity	NPC245866
0.766	Intermediate Similarity	NPC52108
0.766	Intermediate Similarity	NPC193870
0.766	Intermediate Similarity	NPC477818
0.766	Intermediate Similarity	NPC474789
0.766	Intermediate Similarity	NPC471037
0.766	Intermediate Similarity	NPC473742
0.766	Intermediate Similarity	NPC110778
0.766	Intermediate Similarity	NPC141941
0.7653	Intermediate Similarity	NPC473956
0.7653	Intermediate Similarity	NPC475751
0.7647	Intermediate Similarity	NPC477813
0.7647	Intermediate Similarity	NPC157739
0.7647	Intermediate Similarity	NPC119036
0.7647	Intermediate Similarity	NPC470067
0.7647	Intermediate Similarity	NPC470066
0.7647	Intermediate Similarity	NPC477854
0.7647	Intermediate Similarity	NPC469725
0.7642	Intermediate Similarity	NPC64844
0.7642	Intermediate Similarity	NPC470170
0.7642	Intermediate Similarity	NPC470169
0.7642	Intermediate Similarity	NPC42847
0.7642	Intermediate Similarity	NPC475781
0.764	Intermediate Similarity	NPC71152
0.7634	Intermediate Similarity	NPC142163
0.7629	Intermediate Similarity	NPC471900
0.7629	Intermediate Similarity	NPC475664
0.7629	Intermediate Similarity	NPC470542
0.7629	Intermediate Similarity	NPC471952
0.7629	Intermediate Similarity	NPC16377
0.7629	Intermediate Similarity	NPC474719
0.7624	Intermediate Similarity	NPC88009
0.7624	Intermediate Similarity	NPC475178
0.7609	Intermediate Similarity	NPC47808
0.7609	Intermediate Similarity	NPC476176
0.7609	Intermediate Similarity	NPC80530
0.7609	Intermediate Similarity	NPC155924
0.7609	Intermediate Similarity	NPC273410
0.7604	Intermediate Similarity	NPC286153
0.7604	Intermediate Similarity	NPC80590
0.7604	Intermediate Similarity	NPC137306
0.7604	Intermediate Similarity	NPC84121
0.76	Intermediate Similarity	NPC303863

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 NPC299654 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1673
0.2-0.3	4119
0.3-0.4	2276
0.4-0.5	475
0.5-0.6	191
0.6-0.7	213
0.7-0.8	49
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7755	Intermediate Similarity	NPD8035	Phase 2
0.7755	Intermediate Similarity	NPD8034	Phase 2
0.7717	Intermediate Similarity	NPD7525	Registered
0.7684	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD6881	Approved
0.757	Intermediate Similarity	NPD6899	Approved
0.7547	Intermediate Similarity	NPD5739	Approved
0.7547	Intermediate Similarity	NPD6675	Approved
0.7547	Intermediate Similarity	NPD6402	Approved
0.7547	Intermediate Similarity	NPD7128	Approved
0.7477	Intermediate Similarity	NPD5697	Approved
0.7431	Intermediate Similarity	NPD6883	Approved
0.7431	Intermediate Similarity	NPD7290	Approved
0.7431	Intermediate Similarity	NPD7102	Approved
0.7407	Intermediate Similarity	NPD7320	Approved
0.7391	Intermediate Similarity	NPD7503	Approved
0.7364	Intermediate Similarity	NPD6649	Approved
0.7364	Intermediate Similarity	NPD6847	Approved
0.7364	Intermediate Similarity	NPD8130	Phase 1
0.7364	Intermediate Similarity	NPD6617	Approved
0.7364	Intermediate Similarity	NPD6650	Approved
0.7364	Intermediate Similarity	NPD6869	Approved
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6013	Approved
0.7339	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6012	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7327	Intermediate Similarity	NPD6399	Phase 3
0.7315	Intermediate Similarity	NPD5701	Approved
0.7308	Intermediate Similarity	NPD7638	Approved
0.7297	Intermediate Similarity	NPD6882	Approved
0.7297	Intermediate Similarity	NPD8297	Approved
0.7248	Intermediate Similarity	NPD6011	Approved
0.7241	Intermediate Similarity	NPD8033	Approved
0.7238	Intermediate Similarity	NPD7640	Approved
0.7238	Intermediate Similarity	NPD7639	Approved
0.7212	Intermediate Similarity	NPD6083	Phase 2
0.7212	Intermediate Similarity	NPD6084	Phase 2
0.713	Intermediate Similarity	NPD7328	Approved
0.713	Intermediate Similarity	NPD7327	Approved
0.7113	Intermediate Similarity	NPD4788	Approved
0.7097	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5286	Approved
0.7075	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD5285	Approved
0.7069	Intermediate Similarity	NPD7516	Approved
0.7054	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7645	Phase 2
0.7048	Intermediate Similarity	NPD4755	Approved
0.7043	Intermediate Similarity	NPD7115	Discovery
0.7041	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6051	Approved
0.7021	Intermediate Similarity	NPD6116	Phase 1
0.7009	Intermediate Similarity	NPD8377	Approved
0.7009	Intermediate Similarity	NPD8294	Approved
0.699	Remote Similarity	NPD4202	Approved
0.6989	Remote Similarity	NPD6942	Approved
0.6989	Remote Similarity	NPD7339	Approved
0.6949	Remote Similarity	NPD8378	Approved
0.6949	Remote Similarity	NPD8335	Approved
0.6949	Remote Similarity	NPD8380	Approved
0.6949	Remote Similarity	NPD8379	Approved
0.6949	Remote Similarity	NPD8296	Approved
0.6944	Remote Similarity	NPD5226	Approved
0.6944	Remote Similarity	NPD5225	Approved
0.6944	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD5211	Phase 2
0.6944	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD6695	Phase 3
0.6931	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7748	Approved
0.6923	Remote Similarity	NPD7101	Approved
0.6923	Remote Similarity	NPD7100	Approved
0.6916	Remote Similarity	NPD4700	Approved
0.6915	Remote Similarity	NPD6117	Approved
0.6893	Remote Similarity	NPD7515	Phase 2
0.6893	Remote Similarity	NPD7637	Suspended
0.6887	Remote Similarity	NPD7902	Approved
0.6882	Remote Similarity	NPD4784	Approved
0.6882	Remote Similarity	NPD6926	Approved
0.6882	Remote Similarity	NPD6924	Approved
0.6882	Remote Similarity	NPD4785	Approved
0.6881	Remote Similarity	NPD5175	Approved
0.6881	Remote Similarity	NPD5174	Approved
0.6869	Remote Similarity	NPD4786	Approved
0.6857	Remote Similarity	NPD5695	Phase 3
0.6852	Remote Similarity	NPD5223	Approved
0.6842	Remote Similarity	NPD6053	Discontinued
0.6838	Remote Similarity	NPD6335	Approved
0.6822	Remote Similarity	NPD5696	Approved
0.6818	Remote Similarity	NPD5141	Approved
0.6813	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6274	Approved
0.6783	Remote Similarity	NPD8133	Approved
0.6783	Remote Similarity	NPD4632	Approved
0.6771	Remote Similarity	NPD6118	Approved
0.6771	Remote Similarity	NPD6114	Approved
0.6771	Remote Similarity	NPD6115	Approved
0.6771	Remote Similarity	NPD6697	Approved
0.6757	Remote Similarity	NPD6008	Approved
0.6752	Remote Similarity	NPD6317	Approved
0.6748	Remote Similarity	NPD7736	Approved
0.6737	Remote Similarity	NPD6933	Approved
0.6733	Remote Similarity	NPD6409	Approved
0.6733	Remote Similarity	NPD5330	Approved
0.6733	Remote Similarity	NPD6684	Approved
0.6733	Remote Similarity	NPD7521	Approved
0.6733	Remote Similarity	NPD7334	Approved
0.6733	Remote Similarity	NPD7146	Approved
0.6731	Remote Similarity	NPD6079	Approved
0.6731	Remote Similarity	NPD5281	Approved
0.6731	Remote Similarity	NPD5284	Approved
0.6723	Remote Similarity	NPD6319	Approved
0.6721	Remote Similarity	NPD7507	Approved
0.6702	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4195	Approved
0.6699	Remote Similarity	NPD5328	Approved
0.6699	Remote Similarity	NPD4753	Phase 2
0.6698	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6313	Approved
0.6695	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD7152	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6639	Remote Similarity	NPD7492	Approved
0.6637	Remote Similarity	NPD4730	Approved
0.6637	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.6633	Remote Similarity	NPD6928	Phase 2
0.6633	Remote Similarity	NPD4748	Discontinued
0.6633	Remote Similarity	NPD4820	Approved
0.6633	Remote Similarity	NPD4819	Approved
0.6633	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4821	Approved
0.6633	Remote Similarity	NPD6930	Phase 2
0.6633	Remote Similarity	NPD7509	Discontinued
0.6633	Remote Similarity	NPD4822	Approved
0.6633	Remote Similarity	NPD6931	Approved
0.661	Remote Similarity	NPD6009	Approved
0.6607	Remote Similarity	NPD4768	Approved
0.6607	Remote Similarity	NPD4767	Approved
0.6604	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7900	Approved
0.6602	Remote Similarity	NPD6903	Approved
0.6585	Remote Similarity	NPD6616	Approved
0.6583	Remote Similarity	NPD6054	Approved
0.6577	Remote Similarity	NPD4754	Approved
0.6571	Remote Similarity	NPD6411	Approved
0.6569	Remote Similarity	NPD6098	Approved
0.6569	Remote Similarity	NPD3618	Phase 1
0.656	Remote Similarity	NPD7319	Approved
0.6559	Remote Similarity	NPD4787	Phase 1
0.6559	Remote Similarity	NPD7143	Approved
0.6559	Remote Similarity	NPD7144	Approved
0.6557	Remote Similarity	NPD7604	Phase 2
0.6549	Remote Similarity	NPD6412	Phase 2
0.6542	Remote Similarity	NPD4629	Approved
0.6542	Remote Similarity	NPD5210	Approved
0.6538	Remote Similarity	NPD6904	Approved
0.6538	Remote Similarity	NPD6673	Approved
0.6538	Remote Similarity	NPD6080	Approved
0.6535	Remote Similarity	NPD3666	Approved
0.6535	Remote Similarity	NPD3133	Approved
0.6535	Remote Similarity	NPD3665	Phase 1
0.6532	Remote Similarity	NPD7078	Approved
0.6531	Remote Similarity	NPD6929	Approved
0.6529	Remote Similarity	NPD5983	Phase 2
0.6529	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5247	Approved
0.6522	Remote Similarity	NPD5249	Phase 3
0.6522	Remote Similarity	NPD5248	Approved
0.6522	Remote Similarity	NPD4634	Approved
0.6522	Remote Similarity	NPD5250	Approved
0.6522	Remote Similarity	NPD5251	Approved
0.6514	Remote Similarity	NPD4225	Approved
0.6505	Remote Similarity	NPD4250	Approved
0.6505	Remote Similarity	NPD4251	Approved
0.65	Remote Similarity	NPD6435	Approved
0.6491	Remote Similarity	NPD5128	Approved
0.6481	Remote Similarity	NPD5222	Approved
0.6481	Remote Similarity	NPD5221	Approved
0.6481	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6370	Approved
0.6466	Remote Similarity	NPD5215	Approved
0.6466	Remote Similarity	NPD5216	Approved
0.6466	Remote Similarity	NPD5217	Approved
0.6465	Remote Similarity	NPD7514	Phase 3
0.6458	Remote Similarity	NPD3702	Approved
0.6452	Remote Similarity	NPD6922	Approved
0.6452	Remote Similarity	NPD6336	Discontinued
0.6452	Remote Similarity	NPD6923	Approved
0.6446	Remote Similarity	NPD6059	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