NPASS Compound

Structure

CID197701 OpenBabel06191715582D 30 34 0 0 1 0 0 0 0 0999 V2000 -7.7569 1.5571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2711 0.7158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2616 2.0428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3864 -0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2616 -1.8429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9158 0.6233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5790 1.0713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4203 1.5571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2522 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9441 0.0999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9441 3.0142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0823 -1.5697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1029 2.5285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2183 -1.3360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1029 -0.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8561 -1.3182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5790 0.0999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8571 -0.5501 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9441 1.0713 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2616 1.0713 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7854 2.5285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6113 -0.7549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7854 1.5571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1029 1.5571 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4203 -0.3858 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2616 0.0999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9069 -0.3481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6267 3.0142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5814 -0.7041 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 1 23 1 0 0 0 0 2 23 1 0 0 0 0 4 25 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 20 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 9 1 1 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 19 24 1 1 0 0 0 20 24 1 1 0 0 0 20 26 1 0 0 0 0 21 23 1 0 0 0 0 21 28 2 0 0 0 0 22 29 2 0 0 0 0 22 30 1 0 0 0 0 24 3 1 1 0 0 0 25 26 1 1 0 0 0 26 5 1 1 0 0 0 27 6 1 6 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.31
Volume:	453.864
LogP:	5.037
LogD:	4.924
LogS:	-5.25
# Rotatable Bonds:	1
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.47
Synthetic Accessibility Score:	4.582
Fsp3:	0.926
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:	-5.108
MDCK Permeability:	4.689523848355748e-05
Pgp-inhibitor:	0.945
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.373
30% Bioavailability (F30%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	90.29582977294922%
Volume Distribution (VD):	0.981
Pgp-substrate:	2.453927993774414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.56
CYP2C19-inhibitor:	0.146
CYP2C19-substrate:	0.958
CYP2C9-inhibitor:	0.241
CYP2C9-substrate:	0.715
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.812
CYP3A4-inhibitor:	0.536
CYP3A4-substrate:	0.659

ADMET: Excretion

Clearance (CL):	4.931
Half-life (T1/2):	0.402

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.228
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.66
Skin Sensitization:	0.855
Carcinogencity:	0.036
Eye Corrosion:	0.574
Eye Irritation:	0.469
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC197701

Natural Product ID:	NPC197701
*Common Name:**	Cabralelactone
IUPAC Name:	(5S)-5-methyl-5-[(5R,8R,9R,10R,13R,14R,17S)-4,4,8,10,14-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]oxolan-2-one
Synonyms:	Cabralelactone
Standard InCHIKey:	NOLGXQBEFHYZHI-QPBHWVAKSA-N
Standard InCHI:	InChI=1S/C27H42O3/c1-23(2)19-10-15-26(5)20(24(19,3)13-11-21(23)28)8-7-17-18(9-14-25(17,26)4)27(6)16-12-22(29)30-27/h17-20H,7-16H2,1-6H3/t17-,18+,19+,20-,24+,25-,26-,27+/m1/s1
SMILES:	O=C1CC[C@@](O1)(C)[C@H]1CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225315
PubChem CID:	44421647
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1248/cpb.24.1532]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	floral spikes	n.a.	n.a.	PMID[17346076]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21087017]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21087017]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22224661]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22799262]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23290052]
NPO32464	dysoxylum binecteriferum	Species	Meliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[24547740]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	stem barks	n.a.	n.a.	PMID[25666824]
NPO40427	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30106297]
NPO40427	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6619885]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[9873651]
NPO5977	Tylophora crebriflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5977	Tylophora crebriflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2412	Agave lecheguilla	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16547	Boreostereum vibrans	Species	Stereaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6300	Esenbeckia almawillia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5977	Tylophora crebriflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6840	Cassia pudibunda	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	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	16

Activity Type	# Activity
Cell Line	12
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[557037]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	>	100000.0	nM	PMID[557037]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	63500.0	nM	PMID[557037]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	97900.0	nM	PMID[557037]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[557038]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[557038]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[557038]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[557038]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[557039]
NPT401	Cell Line	786-0	Homo sapiens	IC50	>	40000.0	nM	PMID[557039]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	40000.0	nM	PMID[557039]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	40000.0	nM	PMID[557039]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[557037]
NPT27	Others	Unspecified		IC50	=	28500.0	nM	PMID[557037]

☑ 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 NPC197701 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	380
0.1-0.2	4681
0.2-0.3	17045
0.3-0.4	7359
0.4-0.5	6443
0.5-0.6	5079
0.6-0.7	1381
0.7-0.8	288
0.8-0.85	32
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.88	High Similarity	NPC472230
0.88	High Similarity	NPC472229
0.8553	High Similarity	NPC58631
0.8451	Intermediate Similarity	NPC108131
0.8442	Intermediate Similarity	NPC13494
0.8406	Intermediate Similarity	NPC84562
0.8406	Intermediate Similarity	NPC42060
0.8378	Intermediate Similarity	NPC471046
0.8333	Intermediate Similarity	NPC469940
0.831	Intermediate Similarity	NPC474962
0.831	Intermediate Similarity	NPC196197
0.8289	Intermediate Similarity	NPC118987
0.8267	Intermediate Similarity	NPC477918
0.825	Intermediate Similarity	NPC92139
0.8219	Intermediate Similarity	NPC474123
0.8205	Intermediate Similarity	NPC258153
0.8205	Intermediate Similarity	NPC476458
0.8194	Intermediate Similarity	NPC477929
0.8182	Intermediate Similarity	NPC170038
0.8182	Intermediate Similarity	NPC1882
0.8182	Intermediate Similarity	NPC472853
0.8169	Intermediate Similarity	NPC473225
0.8143	Intermediate Similarity	NPC268736
0.8143	Intermediate Similarity	NPC477931
0.8088	Intermediate Similarity	NPC306750
0.8077	Intermediate Similarity	NPC232625
0.8056	Intermediate Similarity	NPC252032
0.8056	Intermediate Similarity	NPC319671
0.8056	Intermediate Similarity	NPC469941
0.8056	Intermediate Similarity	NPC295788
0.8056	Intermediate Similarity	NPC476734
0.8052	Intermediate Similarity	NPC245029
0.8052	Intermediate Similarity	NPC31302
0.8028	Intermediate Similarity	NPC478180
0.8028	Intermediate Similarity	NPC130459
0.8028	Intermediate Similarity	NPC474221
0.8026	Intermediate Similarity	NPC474404
0.8	Intermediate Similarity	NPC72444
0.8	Intermediate Similarity	NPC477934
0.7973	Intermediate Similarity	NPC475230
0.7941	Intermediate Similarity	NPC478126
0.7922	Intermediate Similarity	NPC199965
0.7922	Intermediate Similarity	NPC63020
0.7922	Intermediate Similarity	NPC476732
0.7901	Intermediate Similarity	NPC470223
0.7895	Intermediate Similarity	NPC477933
0.7895	Intermediate Similarity	NPC477932
0.7879	Intermediate Similarity	NPC143597
0.7879	Intermediate Similarity	NPC151464
0.7867	Intermediate Similarity	NPC167702
0.7867	Intermediate Similarity	NPC280026
0.7838	Intermediate Similarity	NPC472309
0.7821	Intermediate Similarity	NPC471475
0.7821	Intermediate Similarity	NPC73013
0.7808	Intermediate Similarity	NPC178541
0.7808	Intermediate Similarity	NPC64466
0.7792	Intermediate Similarity	NPC66105
0.7792	Intermediate Similarity	NPC180199
0.7792	Intermediate Similarity	NPC471151
0.7792	Intermediate Similarity	NPC477919
0.7763	Intermediate Similarity	NPC212733
0.7763	Intermediate Similarity	NPC472311
0.7763	Intermediate Similarity	NPC179858
0.775	Intermediate Similarity	NPC61107
0.775	Intermediate Similarity	NPC24556
0.775	Intermediate Similarity	NPC311642
0.775	Intermediate Similarity	NPC164289
0.775	Intermediate Similarity	NPC477936
0.775	Intermediate Similarity	NPC102156
0.775	Intermediate Similarity	NPC100366
0.775	Intermediate Similarity	NPC477935
0.775	Intermediate Similarity	NPC289486
0.775	Intermediate Similarity	NPC242771
0.775	Intermediate Similarity	NPC148740
0.7738	Intermediate Similarity	NPC472234
0.7738	Intermediate Similarity	NPC472233
0.7733	Intermediate Similarity	NPC279241
0.7733	Intermediate Similarity	NPC109510
0.7733	Intermediate Similarity	NPC248567
0.7727	Intermediate Similarity	NPC184819
0.7722	Intermediate Similarity	NPC261616
0.7703	Intermediate Similarity	NPC477850
0.7692	Intermediate Similarity	NPC185465
0.7681	Intermediate Similarity	NPC84218
0.7674	Intermediate Similarity	NPC228700
0.7671	Intermediate Similarity	NPC281203
0.7671	Intermediate Similarity	NPC100917
0.7671	Intermediate Similarity	NPC469724
0.7671	Intermediate Similarity	NPC31187
0.7662	Intermediate Similarity	NPC4209
0.7654	Intermediate Similarity	NPC217559
0.7654	Intermediate Similarity	NPC268578
0.7654	Intermediate Similarity	NPC292458
0.7654	Intermediate Similarity	NPC15821
0.7632	Intermediate Similarity	NPC472854
0.7632	Intermediate Similarity	NPC55508
0.7632	Intermediate Similarity	NPC477930
0.7632	Intermediate Similarity	NPC96759
0.7625	Intermediate Similarity	NPC280781
0.7625	Intermediate Similarity	NPC48756
0.7619	Intermediate Similarity	NPC28227
0.76	Intermediate Similarity	NPC151018
0.76	Intermediate Similarity	NPC320549
0.76	Intermediate Similarity	NPC478227
0.76	Intermediate Similarity	NPC156277
0.76	Intermediate Similarity	NPC58057
0.7595	Intermediate Similarity	NPC320144
0.7595	Intermediate Similarity	NPC192744
0.7595	Intermediate Similarity	NPC80891
0.7595	Intermediate Similarity	NPC201276
0.7586	Intermediate Similarity	NPC206878
0.7576	Intermediate Similarity	NPC288296
0.7576	Intermediate Similarity	NPC53245
0.7564	Intermediate Similarity	NPC23884
0.7564	Intermediate Similarity	NPC143133
0.7564	Intermediate Similarity	NPC298168
0.7564	Intermediate Similarity	NPC317913
0.7564	Intermediate Similarity	NPC207010
0.7561	Intermediate Similarity	NPC82492
0.7561	Intermediate Similarity	NPC319909
0.7561	Intermediate Similarity	NPC473336
0.7561	Intermediate Similarity	NPC474996
0.7561	Intermediate Similarity	NPC51135
0.7561	Intermediate Similarity	NPC471044
0.7561	Intermediate Similarity	NPC101138
0.7561	Intermediate Similarity	NPC25802
0.7534	Intermediate Similarity	NPC41542
0.7532	Intermediate Similarity	NPC125767
0.7532	Intermediate Similarity	NPC21220
0.7529	Intermediate Similarity	NPC285982
0.7529	Intermediate Similarity	NPC473039
0.75	Intermediate Similarity	NPC474755
0.75	Intermediate Similarity	NPC19311
0.75	Intermediate Similarity	NPC232112
0.75	Intermediate Similarity	NPC310766
0.75	Intermediate Similarity	NPC230047
0.7471	Intermediate Similarity	NPC472231
0.7471	Intermediate Similarity	NPC472232
0.7471	Intermediate Similarity	NPC475700
0.7468	Intermediate Similarity	NPC224802
0.7468	Intermediate Similarity	NPC80089
0.7468	Intermediate Similarity	NPC329117
0.7468	Intermediate Similarity	NPC34046
0.7468	Intermediate Similarity	NPC171426
0.7468	Intermediate Similarity	NPC324700
0.7439	Intermediate Similarity	NPC259173
0.7436	Intermediate Similarity	NPC472486
0.7436	Intermediate Similarity	NPC472487
0.7436	Intermediate Similarity	NPC246445
0.7432	Intermediate Similarity	NPC470956
0.7412	Intermediate Similarity	NPC33398
0.7407	Intermediate Similarity	NPC77311
0.7407	Intermediate Similarity	NPC12933
0.7403	Intermediate Similarity	NPC272359
0.7403	Intermediate Similarity	NPC254340
0.7386	Intermediate Similarity	NPC472223
0.7386	Intermediate Similarity	NPC472224
0.7381	Intermediate Similarity	NPC80700
0.7381	Intermediate Similarity	NPC471042
0.7381	Intermediate Similarity	NPC474448
0.7375	Intermediate Similarity	NPC477287
0.7375	Intermediate Similarity	NPC472310
0.7368	Intermediate Similarity	NPC473267
0.7368	Intermediate Similarity	NPC89310
0.7356	Intermediate Similarity	NPC150383
0.7353	Intermediate Similarity	NPC474105
0.7349	Intermediate Similarity	NPC475509
0.7349	Intermediate Similarity	NPC100391
0.7342	Intermediate Similarity	NPC471035
0.7342	Intermediate Similarity	NPC212661
0.7342	Intermediate Similarity	NPC264602
0.7342	Intermediate Similarity	NPC475031
0.7342	Intermediate Similarity	NPC68828
0.7333	Intermediate Similarity	NPC324607
0.7333	Intermediate Similarity	NPC213178
0.7333	Intermediate Similarity	NPC327728
0.7333	Intermediate Similarity	NPC321732
0.7333	Intermediate Similarity	NPC131892
0.7333	Intermediate Similarity	NPC6120
0.7326	Intermediate Similarity	NPC61688
0.7326	Intermediate Similarity	NPC200580
0.7326	Intermediate Similarity	NPC11611
0.7317	Intermediate Similarity	NPC30583
0.7317	Intermediate Similarity	NPC100297
0.7317	Intermediate Similarity	NPC271163
0.7308	Intermediate Similarity	NPC97534
0.7308	Intermediate Similarity	NPC174964
0.7308	Intermediate Similarity	NPC27349
0.7308	Intermediate Similarity	NPC273366
0.7308	Intermediate Similarity	NPC195155
0.7308	Intermediate Similarity	NPC24014
0.7303	Intermediate Similarity	NPC280877
0.7297	Intermediate Similarity	NPC469868
0.7284	Intermediate Similarity	NPC134227
0.7284	Intermediate Similarity	NPC125366
0.7273	Intermediate Similarity	NPC330659
0.7273	Intermediate Similarity	NPC472226
0.7273	Intermediate Similarity	NPC472225
0.7273	Intermediate Similarity	NPC472237
0.7273	Intermediate Similarity	NPC472238

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 NPC197701 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	4027
0.2-0.3	3427
0.3-0.4	723
0.4-0.5	253
0.5-0.6	223
0.6-0.7	62
0.7-0.8	22
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8592	High Similarity	NPD5777	Approved
0.8406	Intermediate Similarity	NPD4224	Phase 2
0.8333	Intermediate Similarity	NPD6081	Approved
0.8169	Intermediate Similarity	NPD5360	Phase 3
0.8169	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3702	Approved
0.7867	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4789	Approved
0.7662	Intermediate Similarity	NPD6117	Approved
0.76	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4758	Discontinued
0.7564	Intermediate Similarity	NPD6116	Phase 1
0.75	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6115	Approved
0.7468	Intermediate Similarity	NPD6114	Approved
0.7468	Intermediate Similarity	NPD6697	Approved
0.7468	Intermediate Similarity	NPD6118	Approved
0.7467	Intermediate Similarity	NPD4244	Approved
0.7467	Intermediate Similarity	NPD4245	Approved
0.7381	Intermediate Similarity	NPD6098	Approved
0.7333	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3698	Phase 2
0.7303	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5364	Discontinued
0.7241	Intermediate Similarity	NPD5207	Approved
0.7191	Intermediate Similarity	NPD6001	Approved
0.7126	Intermediate Similarity	NPD6904	Approved
0.7126	Intermediate Similarity	NPD6673	Approved
0.7126	Intermediate Similarity	NPD6080	Approved
0.7011	Intermediate Similarity	NPD6903	Approved
0.7011	Intermediate Similarity	NPD5737	Approved
0.7011	Intermediate Similarity	NPD5208	Approved
0.7011	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6672	Approved
0.6977	Remote Similarity	NPD6684	Approved
0.6977	Remote Similarity	NPD7146	Approved
0.6977	Remote Similarity	NPD5330	Approved
0.6977	Remote Similarity	NPD7521	Approved
0.6977	Remote Similarity	NPD6409	Approved
0.6977	Remote Similarity	NPD7334	Approved
0.6966	Remote Similarity	NPD8034	Phase 2
0.6966	Remote Similarity	NPD8035	Phase 2
0.6889	Remote Similarity	NPD6399	Phase 3
0.6875	Remote Similarity	NPD3703	Phase 2
0.686	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4788	Approved
0.6778	Remote Similarity	NPD5693	Phase 1
0.6778	Remote Similarity	NPD6050	Approved
0.6771	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6627	Remote Similarity	NPD3671	Phase 1
0.6596	Remote Similarity	NPD6083	Phase 2
0.6596	Remote Similarity	NPD6084	Phase 2
0.6593	Remote Similarity	NPD5694	Approved
0.6571	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5696	Approved
0.6512	Remote Similarity	NPD4221	Approved
0.6512	Remote Similarity	NPD4223	Phase 3
0.6477	Remote Similarity	NPD5329	Approved
0.6465	Remote Similarity	NPD6008	Approved
0.6429	Remote Similarity	NPD3617	Approved
0.6413	Remote Similarity	NPD5284	Approved
0.6413	Remote Similarity	NPD5281	Approved
0.6395	Remote Similarity	NPD4139	Approved
0.6395	Remote Similarity	NPD4692	Approved
0.6383	Remote Similarity	NPD5695	Phase 3
0.6383	Remote Similarity	NPD5654	Approved
0.6364	Remote Similarity	NPD4786	Approved
0.6364	Remote Similarity	NPD4197	Approved
0.6333	Remote Similarity	NPD3573	Approved
0.6279	Remote Similarity	NPD6928	Phase 2
0.6277	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7900	Approved
0.6269	Remote Similarity	NPD343	Approved
0.6269	Remote Similarity	NPD344	Approved
0.6269	Remote Similarity	NPD345	Approved
0.625	Remote Similarity	NPD3725	Approved
0.625	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3726	Approved
0.625	Remote Similarity	NPD5959	Approved
0.6238	Remote Similarity	NPD6614	Approved
0.6222	Remote Similarity	NPD4689	Approved
0.6222	Remote Similarity	NPD5205	Approved
0.6222	Remote Similarity	NPD4693	Phase 3
0.6222	Remote Similarity	NPD4690	Approved
0.6222	Remote Similarity	NPD4688	Approved
0.6222	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4138	Approved
0.62	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7320	Approved
0.6173	Remote Similarity	NPD4787	Phase 1
0.6173	Remote Similarity	NPD4747	Approved
0.6139	Remote Similarity	NPD6675	Approved
0.6139	Remote Similarity	NPD5739	Approved
0.6139	Remote Similarity	NPD7128	Approved
0.6139	Remote Similarity	NPD6402	Approved
0.6136	Remote Similarity	NPD3667	Approved
0.6133	Remote Similarity	NPD3198	Approved
0.6125	Remote Similarity	NPD229	Approved
0.6117	Remote Similarity	NPD6372	Approved
0.6117	Remote Similarity	NPD6373	Approved
0.6105	Remote Similarity	NPD7748	Approved
0.6082	Remote Similarity	NPD7902	Approved
0.6049	Remote Similarity	NPD4137	Phase 3
0.6047	Remote Similarity	NPD4238	Approved
0.6047	Remote Similarity	NPD4802	Phase 2
0.6044	Remote Similarity	NPD5280	Approved
0.6044	Remote Similarity	NPD4694	Approved
0.6044	Remote Similarity	NPD5690	Phase 2
0.6044	Remote Similarity	NPD3618	Phase 1
0.6023	Remote Similarity	NPD1779	Approved
0.6023	Remote Similarity	NPD1780	Approved
0.6022	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5328	Approved
0.6022	Remote Similarity	NPD6051	Approved
0.6022	Remote Similarity	NPD4753	Phase 2
0.6019	Remote Similarity	NPD6881	Approved
0.6019	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD6649	Approved
0.5976	Remote Similarity	NPD4691	Approved
0.596	Remote Similarity	NPD8418	Phase 2
0.5955	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5733	Approved
0.5934	Remote Similarity	NPD1694	Approved
0.5926	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5697	Approved
0.5922	Remote Similarity	NPD5701	Approved
0.5909	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6883	Approved
0.5905	Remote Similarity	NPD7102	Approved
0.5905	Remote Similarity	NPD7290	Approved
0.59	Remote Similarity	NPD1700	Approved
0.5895	Remote Similarity	NPD7515	Phase 2
0.5895	Remote Similarity	NPD6079	Approved
0.5876	Remote Similarity	NPD4629	Approved
0.5876	Remote Similarity	NPD5210	Approved
0.5865	Remote Similarity	NPD6011	Approved
0.5862	Remote Similarity	NPD4776	Phase 2
0.5862	Remote Similarity	NPD4777	Suspended
0.5859	Remote Similarity	NPD7638	Approved
0.5849	Remote Similarity	NPD6617	Approved
0.5849	Remote Similarity	NPD6847	Approved
0.5849	Remote Similarity	NPD6869	Approved
0.5849	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD8130	Phase 1
0.5833	Remote Similarity	NPD4202	Approved
0.5825	Remote Similarity	NPD6920	Discontinued
0.5816	Remote Similarity	NPD7732	Phase 3
0.5816	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6012	Approved
0.581	Remote Similarity	NPD6014	Approved
0.581	Remote Similarity	NPD6013	Approved
0.58	Remote Similarity	NPD7639	Approved
0.58	Remote Similarity	NPD7640	Approved
0.5795	Remote Similarity	NPD4195	Approved
0.5794	Remote Similarity	NPD6882	Approved
0.5794	Remote Similarity	NPD8297	Approved
0.5765	Remote Similarity	NPD4058	Approved
0.5765	Remote Similarity	NPD4687	Approved
0.575	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD4243	Approved
0.5714	Remote Similarity	NPD5276	Approved
0.5699	Remote Similarity	NPD4623	Approved
0.5699	Remote Similarity	NPD5279	Phase 3
0.5699	Remote Similarity	NPD4519	Discontinued
0.5686	Remote Similarity	NPD7632	Discontinued
0.5679	Remote Similarity	NPD375	Phase 2
0.5676	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.567	Remote Similarity	NPD5133	Approved
0.5664	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4697	Phase 3
0.5657	Remote Similarity	NPD7614	Phase 1
0.5652	Remote Similarity	NPD634	Phase 3
0.5625	Remote Similarity	NPD4096	Approved
0.5616	Remote Similarity	NPD3186	Phase 1
0.5612	Remote Similarity	NPD5707	Approved
0.56	Remote Similarity	NPD4755	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