NPASS Compound

Structure

CID58631 OpenBabel06191715392D 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 2 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 1 6 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:	416.33
Volume:	456.5
LogP:	5.27
LogD:	4.926
LogS:	-5.227
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.523
Synthetic Accessibility Score:	4.607
Fsp3:	0.963
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:	-5.081
MDCK Permeability:	6.311779725365341e-05
Pgp-inhibitor:	0.919
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.518

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	94.45409393310547%
Volume Distribution (VD):	1.033
Pgp-substrate:	2.076296329498291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.38
CYP2C19-inhibitor:	0.107
CYP2C19-substrate:	0.934
CYP2C9-inhibitor:	0.246
CYP2C9-substrate:	0.458
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.757
CYP3A4-inhibitor:	0.4
CYP3A4-substrate:	0.509

ADMET: Excretion

Clearance (CL):	3.898
Half-life (T1/2):	0.194

ADMET: Toxicity

hERG Blockers:	0.197
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.824
Skin Sensitization:	0.944
Carcinogencity:	0.008
Eye Corrosion:	0.879
Eye Irritation:	0.766
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC58631

Natural Product ID:	NPC58631
*Common Name:**	Cabraleahydroxylactone
IUPAC Name:	(5S)-5-[(3R,5R,8R,9R,10R,13R,14R,17S)-3-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-methyloxolan-2-one
Synonyms:	Cabraleahydroxylactone
Standard InCHIKey:	AHDUWGQSZYSNEY-HUOCPXEISA-N
Standard InCHI:	InChI=1S/C27H44O3/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/h17-21,28H,7-16H2,1-6H3/t17-,18+,19+,20-,21-,24+,25-,26-,27+/m1/s1
SMILES:	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@H](CC[C@@]34C)[C@]3(C)CCC(=O)O3)[C@@]2(C)CC[C@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL224197
PubChem CID:	44421648
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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	floral spikes	n.a.	n.a.	PMID[17346076]
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]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	leaves, twigs, and fruits	Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam	2010-Jan	PMID[23301897]
NPO32464	dysoxylum binecteriferum	Species	Meliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[24547740]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31621322]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[9873651]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	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]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4720	Aglaia perviridis	Species	Meliaceae	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
ED50	2
IC50	12

Activity Type	# Activity
Cell Line	9
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100000.0	nM	PMID[557232]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[557232]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[557232]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	>	100000.0	nM	PMID[557232]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	uM	PMID[557233]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[557234]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[557234]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[557234]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[557234]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[557232]
NPT27	Others	Unspecified		IC50	=	20600.0	nM	PMID[557232]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	ED50	>	20.0	uM	PMID[557233]

☑ 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 NPC58631 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	342
0.1-0.2	3021
0.2-0.3	12176
0.3-0.4	11583
0.4-0.5	5620
0.5-0.6	5350
0.6-0.7	3549
0.7-0.8	888
0.8-0.85	130
0.85-0.9	34
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.92	High Similarity	NPC212733
0.9079	High Similarity	NPC4209
0.9067	High Similarity	NPC167702
0.9067	High Similarity	NPC280026
0.8987	High Similarity	NPC280781
0.8987	High Similarity	NPC48756
0.8974	High Similarity	NPC201276
0.8974	High Similarity	NPC80891
0.8961	High Similarity	NPC298168
0.8961	High Similarity	NPC207010
0.8961	High Similarity	NPC143133
0.8961	High Similarity	NPC317913
0.8875	High Similarity	NPC289486
0.8875	High Similarity	NPC13494
0.8875	High Similarity	NPC61107
0.8861	High Similarity	NPC261616
0.8846	High Similarity	NPC34046
0.8846	High Similarity	NPC324700
0.8846	High Similarity	NPC171426
0.8846	High Similarity	NPC224802
0.8846	High Similarity	NPC80089
0.875	High Similarity	NPC12933
0.8734	High Similarity	NPC320144
0.8721	High Similarity	NPC472232
0.8721	High Similarity	NPC472231
0.8718	High Similarity	NPC23884
0.8684	High Similarity	NPC232112
0.8675	High Similarity	NPC92139
0.8667	High Similarity	NPC477929
0.8659	High Similarity	NPC473336
0.8659	High Similarity	NPC471044
0.8659	High Similarity	NPC474996
0.8608	High Similarity	NPC185465
0.859	High Similarity	NPC472487
0.859	High Similarity	NPC472486
0.8553	High Similarity	NPC469940
0.8553	High Similarity	NPC89310
0.8553	High Similarity	NPC151018
0.8553	High Similarity	NPC156277
0.8553	High Similarity	NPC197701
0.8553	High Similarity	NPC320549
0.8553	High Similarity	NPC58057
0.8533	High Similarity	NPC469941
0.8533	High Similarity	NPC196197
0.8533	High Similarity	NPC319671
0.8533	High Similarity	NPC476734
0.8533	High Similarity	NPC252032
0.8481	Intermediate Similarity	NPC474404
0.8481	Intermediate Similarity	NPC307865
0.8481	Intermediate Similarity	NPC475031
0.8462	Intermediate Similarity	NPC125767
0.8462	Intermediate Similarity	NPC273366
0.8462	Intermediate Similarity	NPC195155
0.8462	Intermediate Similarity	NPC21220
0.8462	Intermediate Similarity	NPC97534
0.8462	Intermediate Similarity	NPC174964
0.8452	Intermediate Similarity	NPC80700
0.8434	Intermediate Similarity	NPC319909
0.8434	Intermediate Similarity	NPC473299
0.8427	Intermediate Similarity	NPC116683
0.8415	Intermediate Similarity	NPC242771
0.8415	Intermediate Similarity	NPC121121
0.8415	Intermediate Similarity	NPC311642
0.8415	Intermediate Similarity	NPC30583
0.8415	Intermediate Similarity	NPC164289
0.8415	Intermediate Similarity	NPC100366
0.8395	Intermediate Similarity	NPC477851
0.8375	Intermediate Similarity	NPC329117
0.8375	Intermediate Similarity	NPC199965
0.8375	Intermediate Similarity	NPC476732
0.8372	Intermediate Similarity	NPC61688
0.8354	Intermediate Similarity	NPC5767
0.8354	Intermediate Similarity	NPC477932
0.8354	Intermediate Similarity	NPC471046
0.8354	Intermediate Similarity	NPC477933
0.8354	Intermediate Similarity	NPC475742
0.8333	Intermediate Similarity	NPC254340
0.8333	Intermediate Similarity	NPC62572
0.8313	Intermediate Similarity	NPC111582
0.8313	Intermediate Similarity	NPC477285
0.8295	Intermediate Similarity	NPC470224
0.8293	Intermediate Similarity	NPC190940
0.8293	Intermediate Similarity	NPC50658
0.8289	Intermediate Similarity	NPC327728
0.8289	Intermediate Similarity	NPC213178
0.8289	Intermediate Similarity	NPC6120
0.8289	Intermediate Similarity	NPC131892
0.8272	Intermediate Similarity	NPC220379
0.8272	Intermediate Similarity	NPC245029
0.8272	Intermediate Similarity	NPC73013
0.8272	Intermediate Similarity	NPC31302
0.8267	Intermediate Similarity	NPC41542
0.825	Intermediate Similarity	NPC477918
0.825	Intermediate Similarity	NPC477919
0.825	Intermediate Similarity	NPC180199
0.825	Intermediate Similarity	NPC221420
0.825	Intermediate Similarity	NPC212453
0.8235	Intermediate Similarity	NPC12774
0.8235	Intermediate Similarity	NPC472272
0.8228	Intermediate Similarity	NPC477934
0.8205	Intermediate Similarity	NPC109510
0.8202	Intermediate Similarity	NPC470424
0.8193	Intermediate Similarity	NPC286719
0.8193	Intermediate Similarity	NPC148740
0.8193	Intermediate Similarity	NPC477935
0.8193	Intermediate Similarity	NPC477286
0.8193	Intermediate Similarity	NPC102156
0.8182	Intermediate Similarity	NPC477850
0.8171	Intermediate Similarity	NPC472853
0.8161	Intermediate Similarity	NPC472234
0.8161	Intermediate Similarity	NPC472233
0.8161	Intermediate Similarity	NPC200580
0.8148	Intermediate Similarity	NPC471045
0.8148	Intermediate Similarity	NPC31031
0.8148	Intermediate Similarity	NPC472608
0.8148	Intermediate Similarity	NPC243594
0.814	Intermediate Similarity	NPC252714
0.814	Intermediate Similarity	NPC33768
0.8133	Intermediate Similarity	NPC42060
0.8133	Intermediate Similarity	NPC84562
0.8132	Intermediate Similarity	NPC253586
0.8118	Intermediate Similarity	NPC264317
0.8118	Intermediate Similarity	NPC477445
0.8118	Intermediate Similarity	NPC294438
0.8101	Intermediate Similarity	NPC55508
0.8101	Intermediate Similarity	NPC477930
0.8095	Intermediate Similarity	NPC292458
0.8095	Intermediate Similarity	NPC259173
0.8095	Intermediate Similarity	NPC217559
0.8095	Intermediate Similarity	NPC268578
0.8095	Intermediate Similarity	NPC471037
0.809	Intermediate Similarity	NPC476189
0.8072	Intermediate Similarity	NPC474870
0.8072	Intermediate Similarity	NPC271572
0.8072	Intermediate Similarity	NPC73515
0.8068	Intermediate Similarity	NPC77756
0.8068	Intermediate Similarity	NPC470114
0.8068	Intermediate Similarity	NPC185529
0.8068	Intermediate Similarity	NPC472146
0.8052	Intermediate Similarity	NPC64466
0.8049	Intermediate Similarity	NPC476176
0.8046	Intermediate Similarity	NPC4309
0.8046	Intermediate Similarity	NPC471221
0.8046	Intermediate Similarity	NPC474719
0.8025	Intermediate Similarity	NPC171658
0.8025	Intermediate Similarity	NPC471151
0.8023	Intermediate Similarity	NPC215968
0.8023	Intermediate Similarity	NPC302111
0.8023	Intermediate Similarity	NPC103782
0.8023	Intermediate Similarity	NPC114378
0.8023	Intermediate Similarity	NPC155531
0.8023	Intermediate Similarity	NPC2783
0.8	Intermediate Similarity	NPC91387
0.8	Intermediate Similarity	NPC159789
0.8	Intermediate Similarity	NPC303863
0.8	Intermediate Similarity	NPC270306
0.8	Intermediate Similarity	NPC230047
0.8	Intermediate Similarity	NPC477434
0.8	Intermediate Similarity	NPC291310
0.8	Intermediate Similarity	NPC34984
0.8	Intermediate Similarity	NPC179858
0.8	Intermediate Similarity	NPC471720
0.8	Intermediate Similarity	NPC186851
0.8	Intermediate Similarity	NPC19311
0.8	Intermediate Similarity	NPC472311
0.8	Intermediate Similarity	NPC25037
0.8	Intermediate Similarity	NPC231680
0.8	Intermediate Similarity	NPC206878
0.7979	Intermediate Similarity	NPC213528
0.7979	Intermediate Similarity	NPC244969
0.7978	Intermediate Similarity	NPC52756
0.7978	Intermediate Similarity	NPC160506
0.7978	Intermediate Similarity	NPC475416
0.7978	Intermediate Similarity	NPC475878
0.7976	Intermediate Similarity	NPC268040
0.7976	Intermediate Similarity	NPC202688
0.7976	Intermediate Similarity	NPC154043
0.7976	Intermediate Similarity	NPC60018
0.7976	Intermediate Similarity	NPC477936
0.7976	Intermediate Similarity	NPC317066
0.7976	Intermediate Similarity	NPC328007
0.7975	Intermediate Similarity	NPC310766
0.7957	Intermediate Similarity	NPC108371
0.7955	Intermediate Similarity	NPC471459
0.7955	Intermediate Similarity	NPC67653
0.7955	Intermediate Similarity	NPC56962
0.7955	Intermediate Similarity	NPC24705
0.7952	Intermediate Similarity	NPC206735
0.7952	Intermediate Similarity	NPC470609
0.7949	Intermediate Similarity	NPC108131
0.7949	Intermediate Similarity	NPC282454
0.7931	Intermediate Similarity	NPC269360
0.7931	Intermediate Similarity	NPC239938
0.7931	Intermediate Similarity	NPC264005
0.7912	Intermediate Similarity	NPC470031
0.7912	Intermediate Similarity	NPC287354
0.7912	Intermediate Similarity	NPC62407
0.7912	Intermediate Similarity	NPC279974
0.7907	Intermediate Similarity	NPC473350
0.7895	Intermediate Similarity	NPC268736

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 NPC58631 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	3309
0.2-0.3	3705
0.3-0.4	1091
0.4-0.5	258
0.5-0.6	218
0.6-0.7	154
0.7-0.8	20
0.8-0.85	8
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9079	High Similarity	NPD6117	Approved
0.9067	High Similarity	NPD6113	Clinical (unspecified phase)
0.8961	High Similarity	NPD6116	Phase 1
0.8846	High Similarity	NPD6115	Approved
0.8846	High Similarity	NPD6118	Approved
0.8846	High Similarity	NPD6697	Approved
0.8846	High Similarity	NPD6114	Approved
0.8553	High Similarity	NPD4808	Clinical (unspecified phase)
0.8553	High Similarity	NPD4809	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD3702	Approved
0.8158	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD5360	Phase 3
0.8118	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD5777	Approved
0.8	Intermediate Similarity	NPD3703	Phase 2
0.7978	Intermediate Similarity	NPD8034	Phase 2
0.7978	Intermediate Similarity	NPD8035	Phase 2
0.7949	Intermediate Similarity	NPD4789	Approved
0.7949	Intermediate Similarity	NPD4245	Approved
0.7949	Intermediate Similarity	NPD4244	Approved
0.7895	Intermediate Similarity	NPD4224	Phase 2
0.7848	Intermediate Similarity	NPD6081	Approved
0.7821	Intermediate Similarity	NPD3698	Phase 2
0.7763	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4758	Discontinued
0.7595	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3671	Phase 1
0.7326	Intermediate Similarity	NPD6928	Phase 2
0.7312	Intermediate Similarity	NPD6399	Phase 3
0.7294	Intermediate Similarity	NPD5364	Discontinued
0.7284	Intermediate Similarity	NPD4787	Phase 1
0.7079	Intermediate Similarity	NPD4788	Approved
0.7059	Intermediate Similarity	NPD7320	Approved
0.7041	Intermediate Similarity	NPD8418	Phase 2
0.7033	Intermediate Similarity	NPD3618	Phase 1
0.703	Intermediate Similarity	NPD6402	Approved
0.703	Intermediate Similarity	NPD6675	Approved
0.703	Intermediate Similarity	NPD5739	Approved
0.703	Intermediate Similarity	NPD7128	Approved
0.7	Intermediate Similarity	NPD4786	Approved
0.699	Remote Similarity	NPD6372	Approved
0.699	Remote Similarity	NPD6373	Approved
0.6989	Remote Similarity	NPD5328	Approved
0.6979	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7638	Approved
0.6931	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6881	Approved
0.6893	Remote Similarity	NPD6899	Approved
0.6883	Remote Similarity	NPD3198	Approved
0.6875	Remote Similarity	NPD7748	Approved
0.6869	Remote Similarity	NPD7639	Approved
0.6869	Remote Similarity	NPD7640	Approved
0.6857	Remote Similarity	NPD6649	Approved
0.6857	Remote Similarity	NPD6650	Approved
0.6842	Remote Similarity	NPD6079	Approved
0.6842	Remote Similarity	NPD7515	Phase 2
0.6837	Remote Similarity	NPD6084	Phase 2
0.6837	Remote Similarity	NPD7902	Approved
0.6837	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD1700	Approved
0.6796	Remote Similarity	NPD5697	Approved
0.6796	Remote Similarity	NPD5701	Approved
0.6778	Remote Similarity	NPD3667	Approved
0.6771	Remote Similarity	NPD4202	Approved
0.6762	Remote Similarity	NPD6883	Approved
0.6762	Remote Similarity	NPD7102	Approved
0.6762	Remote Similarity	NPD7290	Approved
0.6742	Remote Similarity	NPD7525	Registered
0.6733	Remote Similarity	NPD7632	Discontinued
0.6731	Remote Similarity	NPD6011	Approved
0.6702	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6903	Approved
0.6701	Remote Similarity	NPD6001	Approved
0.6699	Remote Similarity	NPD6008	Approved
0.6698	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6869	Approved
0.6698	Remote Similarity	NPD6617	Approved
0.6698	Remote Similarity	NPD6847	Approved
0.6698	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6636	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.66	Remote Similarity	NPD5696	Approved
0.6566	Remote Similarity	NPD4697	Phase 3
0.6545	Remote Similarity	NPD7115	Discovery
0.6538	Remote Similarity	NPD6920	Discontinued
0.6531	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7900	Approved
0.6526	Remote Similarity	NPD5737	Approved
0.6526	Remote Similarity	NPD6672	Approved
0.65	Remote Similarity	NPD4755	Approved
0.6489	Remote Similarity	NPD6098	Approved
0.6465	Remote Similarity	NPD5695	Phase 3
0.646	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3666	Approved
0.6452	Remote Similarity	NPD3665	Phase 1
0.6452	Remote Similarity	NPD3133	Approved
0.6447	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8171	Discontinued
0.6429	Remote Similarity	NPD229	Approved
0.6422	Remote Similarity	NPD8133	Approved
0.6415	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5222	Approved
0.64	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5221	Approved
0.6392	Remote Similarity	NPD5207	Approved
0.6373	Remote Similarity	NPD5285	Approved
0.6373	Remote Similarity	NPD5286	Approved
0.6373	Remote Similarity	NPD4696	Approved
0.6373	Remote Similarity	NPD4700	Approved
0.6339	Remote Similarity	NPD6335	Approved
0.6337	Remote Similarity	NPD5173	Approved
0.6333	Remote Similarity	NPD4802	Phase 2
0.6333	Remote Similarity	NPD4238	Approved
0.6316	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5223	Approved
0.6306	Remote Similarity	NPD6868	Approved
0.6306	Remote Similarity	NPD6274	Approved
0.6306	Remote Similarity	NPD6940	Discontinued
0.6293	Remote Similarity	NPD7492	Approved
0.6289	Remote Similarity	NPD6673	Approved
0.6289	Remote Similarity	NPD4753	Phase 2
0.6289	Remote Similarity	NPD6904	Approved
0.6289	Remote Similarity	NPD6080	Approved
0.6283	Remote Similarity	NPD7101	Approved
0.6283	Remote Similarity	NPD7100	Approved
0.6273	Remote Similarity	NPD4632	Approved
0.6273	Remote Similarity	NPD8298	Phase 2
0.6271	Remote Similarity	NPD7736	Approved
0.6262	Remote Similarity	NPD6415	Discontinued
0.625	Remote Similarity	NPD6317	Approved
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD5226	Approved
0.6239	Remote Similarity	NPD7507	Approved
0.6239	Remote Similarity	NPD6616	Approved
0.6237	Remote Similarity	NPD4223	Phase 3
0.6237	Remote Similarity	NPD4221	Approved
0.6234	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6059	Approved
0.6228	Remote Similarity	NPD6054	Approved
0.6211	Remote Similarity	NPD5329	Approved
0.6204	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6313	Approved
0.6195	Remote Similarity	NPD6314	Approved
0.619	Remote Similarity	NPD5174	Approved
0.619	Remote Similarity	NPD5175	Approved
0.619	Remote Similarity	NPD4754	Approved
0.6186	Remote Similarity	NPD5208	Approved
0.6186	Remote Similarity	NPD8293	Discontinued
0.6186	Remote Similarity	NPD7078	Approved
0.618	Remote Similarity	NPD7339	Approved
0.618	Remote Similarity	NPD6942	Approved
0.6174	Remote Similarity	NPD6908	Approved
0.6174	Remote Similarity	NPD6909	Approved
0.617	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.617	Remote Similarity	NPD3669	Approved
0.6162	Remote Similarity	NPD5284	Approved
0.6162	Remote Similarity	NPD5281	Approved
0.6154	Remote Similarity	NPD3617	Approved
0.6147	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5279	Phase 3
0.6139	Remote Similarity	NPD5210	Approved
0.6139	Remote Similarity	NPD4629	Approved
0.6139	Remote Similarity	NPD7991	Discontinued
0.6132	Remote Similarity	NPD5141	Approved
0.6129	Remote Similarity	NPD4139	Approved
0.6129	Remote Similarity	NPD1780	Approved
0.6129	Remote Similarity	NPD1779	Approved
0.6129	Remote Similarity	NPD4692	Approved
0.6121	Remote Similarity	NPD6370	Approved
0.6117	Remote Similarity	NPD4225	Approved
0.6106	Remote Similarity	NPD6009	Approved
0.6105	Remote Similarity	NPD3668	Phase 3
0.6105	Remote Similarity	NPD4197	Approved
0.6087	Remote Similarity	NPD6319	Approved
0.6087	Remote Similarity	NPD7645	Phase 2
0.6083	Remote Similarity	NPD7319	Approved
0.6082	Remote Similarity	NPD3573	Approved
0.6075	Remote Similarity	NPD4767	Approved
0.6075	Remote Similarity	NPD4768	Approved
0.6071	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD7604	Phase 2
0.6047	Remote Similarity	NPD6705	Phase 1
0.6042	Remote Similarity	NPD1694	Approved
0.6038	Remote Similarity	NPD6052	Approved
0.6034	Remote Similarity	NPD6016	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