NPASS Compound

Structure

CID13385 OpenBabel06191715342D 34 37 0 0 1 0 0 0 0 0999 V2000 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3022 6.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6549 6.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6842 4.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3751 3.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7302 2.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9456 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0369 4.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7279 4.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6758 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3240 6.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0150 5.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3970 3.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0880 2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 19 2 0 0 0 0 8 34 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 12 25 2 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 20 5 1 1 0 0 0 20 22 1 0 0 0 0 21 11 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 24 29 1 1 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 26 31 2 0 0 0 0 27 30 1 0 0 0 0 27 32 2 0 0 0 0 27 34 1 0 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 30 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	517.825
LogP:	6.808
LogD:	6.236
LogS:	-5.422
# Rotatable Bonds:	8
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.276
Synthetic Accessibility Score:	4.993
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.758
MDCK Permeability:	3.282745819888078e-05
Pgp-inhibitor:	0.911
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.117

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.801
Plasma Protein Binding (PPB):	97.4471206665039%
Volume Distribution (VD):	1.104
Pgp-substrate:	2.4397151470184326%

ADMET: Metabolism

CYP1A2-inhibitor:	0.093
CYP1A2-substrate:	0.618
CYP2C19-inhibitor:	0.53
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.599
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.097
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.767

ADMET: Excretion

Clearance (CL):	7.761
Half-life (T1/2):	0.026

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.614
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.641
Maximum Recommended Daily Dose:	0.062
Skin Sensitization:	0.125
Carcinogencity:	0.163
Eye Corrosion:	0.145
Eye Irritation:	0.026
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC13385

Natural Product ID:	NPC13385
*Common Name:**	2-Ethoxycarbonyl-2Beta-Hydroxy-A-Nor-Ergosta-5,24(28)-Dien-4-One
IUPAC Name:	ethyl (2S,3aR,3bS,5aR,6R,8aS,8bS)-2-hydroxy-3a,5a-dimethyl-6-[(2R)-6-methyl-5-methylideneheptan-2-yl]-1-oxo-3,3b,4,5,6,7,8,8a,8b,9-decahydroindeno[5,4-e]indene-2-carboxylate
Synonyms:
Standard InCHIKey:	SDACHZAENXVBHJ-BZWIQRMTSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-8-34-27(32)30(33)17-29(7)24-15-16-28(6)22(20(5)10-9-19(4)18(2)3)13-14-23(28)21(24)11-12-25(29)26(30)31/h12,18,20-24,33H,4,8-11,13-17H2,1-3,5-7H3/t20-,21+,22-,23+,24+,28-,29-,30+/m1/s1
SMILES:	CCOC(=O)[C@]1(O)C[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CCC(=C)C(C)C)C)C)C1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470866
PubChem CID:	16086577
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003568] Androstane steroids

*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
NPO25032	Haliclona oculata	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989529]
NPO25032	Haliclona oculata	Species	Chalinidae	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	7

Activity Type	# Activity
Cell Line	4
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[553020]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[553020]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[553020]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.32	ug.mL-1	PMID[553020]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.47	ug.mL-1	PMID[553020]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	0.73	ug.mL-1	PMID[553020]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[553020]

☑ 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 NPC13385 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	205
0.1-0.2	1230
0.2-0.3	5443
0.3-0.4	11024
0.4-0.5	10521
0.5-0.6	7091
0.6-0.7	5859
0.7-0.8	1297
0.8-0.85	22
0.85-0.9	0
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9691	High Similarity	NPC474330
0.9691	High Similarity	NPC474207
0.9688	High Similarity	NPC475867
0.9688	High Similarity	NPC270155
0.8317	Intermediate Similarity	NPC472733
0.8317	Intermediate Similarity	NPC472734
0.8286	Intermediate Similarity	NPC255309
0.8286	Intermediate Similarity	NPC235889
0.8235	Intermediate Similarity	NPC472731
0.8235	Intermediate Similarity	NPC472732
0.8224	Intermediate Similarity	NPC469508
0.8208	Intermediate Similarity	NPC181265
0.8208	Intermediate Similarity	NPC96377
0.8155	Intermediate Similarity	NPC177680
0.8155	Intermediate Similarity	NPC153776
0.8155	Intermediate Similarity	NPC472730
0.8155	Intermediate Similarity	NPC472729
0.8148	Intermediate Similarity	NPC470257
0.8131	Intermediate Similarity	NPC475294
0.8103	Intermediate Similarity	NPC473255
0.8095	Intermediate Similarity	NPC473928
0.8091	Intermediate Similarity	NPC191620
0.8081	Intermediate Similarity	NPC474570
0.8077	Intermediate Similarity	NPC472727
0.8077	Intermediate Similarity	NPC472728
0.8073	Intermediate Similarity	NPC37116
0.8073	Intermediate Similarity	NPC473627
0.8058	Intermediate Similarity	NPC27105
0.8021	Intermediate Similarity	NPC477373
0.802	Intermediate Similarity	NPC109414
0.8018	Intermediate Similarity	NPC194100
0.8	Intermediate Similarity	NPC470961
0.8	Intermediate Similarity	NPC470921
0.8	Intermediate Similarity	NPC43775
0.8	Intermediate Similarity	NPC475099
0.7982	Intermediate Similarity	NPC474901
0.7982	Intermediate Similarity	NPC475941
0.7982	Intermediate Similarity	NPC258543
0.7982	Intermediate Similarity	NPC241927
0.7982	Intermediate Similarity	NPC304495
0.7981	Intermediate Similarity	NPC203388
0.7981	Intermediate Similarity	NPC99657
0.7981	Intermediate Similarity	NPC472687
0.7981	Intermediate Similarity	NPC197386
0.7981	Intermediate Similarity	NPC471330
0.7981	Intermediate Similarity	NPC471331
0.7981	Intermediate Similarity	NPC147954
0.7966	Intermediate Similarity	NPC470882
0.7966	Intermediate Similarity	NPC473265
0.7966	Intermediate Similarity	NPC473253
0.7965	Intermediate Similarity	NPC239273
0.7965	Intermediate Similarity	NPC471854
0.7963	Intermediate Similarity	NPC58370
0.7963	Intermediate Similarity	NPC220974
0.7963	Intermediate Similarity	NPC472925
0.7963	Intermediate Similarity	NPC44063
0.7963	Intermediate Similarity	NPC43285
0.7961	Intermediate Similarity	NPC328162
0.7961	Intermediate Similarity	NPC96859
0.7961	Intermediate Similarity	NPC305483
0.7941	Intermediate Similarity	NPC124207
0.7928	Intermediate Similarity	NPC221144
0.7928	Intermediate Similarity	NPC100267
0.7928	Intermediate Similarity	NPC475524
0.7925	Intermediate Similarity	NPC119601
0.7925	Intermediate Similarity	NPC473163
0.7925	Intermediate Similarity	NPC308351
0.7925	Intermediate Similarity	NPC271266
0.7925	Intermediate Similarity	NPC308726
0.7909	Intermediate Similarity	NPC5284
0.7909	Intermediate Similarity	NPC239097
0.7909	Intermediate Similarity	NPC29133
0.7905	Intermediate Similarity	NPC316964
0.7905	Intermediate Similarity	NPC476274
0.79	Intermediate Similarity	NPC305039
0.79	Intermediate Similarity	NPC215029
0.79	Intermediate Similarity	NPC476733
0.7895	Intermediate Similarity	NPC257457
0.7895	Intermediate Similarity	NPC311554
0.7895	Intermediate Similarity	NPC329736
0.7885	Intermediate Similarity	NPC43747
0.7879	Intermediate Similarity	NPC167877
0.7879	Intermediate Similarity	NPC96496
0.7876	Intermediate Similarity	NPC270929
0.7876	Intermediate Similarity	NPC190286
0.787	Intermediate Similarity	NPC471333
0.787	Intermediate Similarity	NPC471332
0.7864	Intermediate Similarity	NPC470016
0.7864	Intermediate Similarity	NPC469599
0.7864	Intermediate Similarity	NPC317586
0.7863	Intermediate Similarity	NPC120724
0.7857	Intermediate Similarity	NPC472926
0.7857	Intermediate Similarity	NPC472929
0.785	Intermediate Similarity	NPC264048
0.7845	Intermediate Similarity	NPC46570
0.7843	Intermediate Similarity	NPC474807
0.7838	Intermediate Similarity	NPC231589
0.7838	Intermediate Similarity	NPC118860
0.7838	Intermediate Similarity	NPC214797
0.7833	Intermediate Similarity	NPC470880
0.783	Intermediate Similarity	NPC163372
0.783	Intermediate Similarity	NPC472924
0.783	Intermediate Similarity	NPC473514
0.783	Intermediate Similarity	NPC476240
0.783	Intermediate Similarity	NPC476223
0.783	Intermediate Similarity	NPC224720
0.783	Intermediate Similarity	NPC99411
0.783	Intermediate Similarity	NPC302537
0.7826	Intermediate Similarity	NPC61520
0.7826	Intermediate Similarity	NPC473203
0.7818	Intermediate Similarity	NPC10064
0.7818	Intermediate Similarity	NPC2766
0.7818	Intermediate Similarity	NPC170221
0.7818	Intermediate Similarity	NPC41405
0.7812	Intermediate Similarity	NPC477372
0.781	Intermediate Similarity	NPC222011
0.7807	Intermediate Similarity	NPC470959
0.7807	Intermediate Similarity	NPC472934
0.7807	Intermediate Similarity	NPC476965
0.7788	Intermediate Similarity	NPC469528
0.7788	Intermediate Similarity	NPC328371
0.7788	Intermediate Similarity	NPC469369
0.7788	Intermediate Similarity	NPC21681
0.7788	Intermediate Similarity	NPC472675
0.7788	Intermediate Similarity	NPC471398
0.7788	Intermediate Similarity	NPC474181
0.7788	Intermediate Similarity	NPC42042
0.7778	Intermediate Similarity	NPC471293
0.7778	Intermediate Similarity	NPC228669
0.7778	Intermediate Similarity	NPC107493
0.7778	Intermediate Similarity	NPC137657
0.7778	Intermediate Similarity	NPC164835
0.7768	Intermediate Similarity	NPC170487
0.7768	Intermediate Similarity	NPC280782
0.7768	Intermediate Similarity	NPC475970
0.7768	Intermediate Similarity	NPC71348
0.7767	Intermediate Similarity	NPC166906
0.7759	Intermediate Similarity	NPC474585
0.7757	Intermediate Similarity	NPC473424
0.7757	Intermediate Similarity	NPC163249
0.7757	Intermediate Similarity	NPC87351
0.7748	Intermediate Similarity	NPC6206
0.7745	Intermediate Similarity	NPC218301
0.7739	Intermediate Similarity	NPC153440
0.7736	Intermediate Similarity	NPC167974
0.7736	Intermediate Similarity	NPC241221
0.7736	Intermediate Similarity	NPC474720
0.7727	Intermediate Similarity	NPC318363
0.7727	Intermediate Similarity	NPC475418
0.7727	Intermediate Similarity	NPC220155
0.7727	Intermediate Similarity	NPC473482
0.7723	Intermediate Similarity	NPC310010
0.7723	Intermediate Similarity	NPC262043
0.7723	Intermediate Similarity	NPC326627
0.7719	Intermediate Similarity	NPC176840
0.7719	Intermediate Similarity	NPC148458
0.7719	Intermediate Similarity	NPC207217
0.7714	Intermediate Similarity	NPC69385
0.7706	Intermediate Similarity	NPC292588
0.7706	Intermediate Similarity	NPC475494
0.7706	Intermediate Similarity	NPC196528
0.7706	Intermediate Similarity	NPC470267
0.7706	Intermediate Similarity	NPC472935
0.77	Intermediate Similarity	NPC136948
0.7699	Intermediate Similarity	NPC250109
0.7692	Intermediate Similarity	NPC469995
0.7692	Intermediate Similarity	NPC471999
0.7692	Intermediate Similarity	NPC472469
0.7692	Intermediate Similarity	NPC318282
0.7692	Intermediate Similarity	NPC174948
0.7692	Intermediate Similarity	NPC472000
0.7692	Intermediate Similarity	NPC173875
0.7692	Intermediate Similarity	NPC171395
0.7685	Intermediate Similarity	NPC117185
0.7685	Intermediate Similarity	NPC470954
0.7685	Intermediate Similarity	NPC236390
0.7685	Intermediate Similarity	NPC179208
0.7685	Intermediate Similarity	NPC111323
0.7685	Intermediate Similarity	NPC311612
0.7685	Intermediate Similarity	NPC36321
0.7679	Intermediate Similarity	NPC472928
0.7677	Intermediate Similarity	NPC29447
0.7677	Intermediate Similarity	NPC469948
0.7677	Intermediate Similarity	NPC474680
0.7672	Intermediate Similarity	NPC5292
0.7672	Intermediate Similarity	NPC472933
0.7672	Intermediate Similarity	NPC319570
0.7672	Intermediate Similarity	NPC264954
0.767	Intermediate Similarity	NPC25750
0.767	Intermediate Similarity	NPC477436
0.767	Intermediate Similarity	NPC206810
0.767	Intermediate Similarity	NPC477435
0.7664	Intermediate Similarity	NPC124211
0.7658	Intermediate Similarity	NPC475065
0.7658	Intermediate Similarity	NPC214644
0.7653	Intermediate Similarity	NPC470015
0.7653	Intermediate Similarity	NPC168188
0.7652	Intermediate Similarity	NPC470492
0.7652	Intermediate Similarity	NPC472927
0.7652	Intermediate Similarity	NPC286528

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 NPC13385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1620
0.2-0.3	4021
0.3-0.4	2258
0.4-0.5	607
0.5-0.6	224
0.6-0.7	124
0.7-0.8	124
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD6084	Phase 2
0.8235	Intermediate Similarity	NPD6083	Phase 2
0.8224	Intermediate Similarity	NPD7320	Approved
0.8218	Intermediate Similarity	NPD5695	Phase 3
0.8091	Intermediate Similarity	NPD8297	Approved
0.8056	Intermediate Similarity	NPD6899	Approved
0.8056	Intermediate Similarity	NPD6881	Approved
0.8037	Intermediate Similarity	NPD6402	Approved
0.8037	Intermediate Similarity	NPD7128	Approved
0.8037	Intermediate Similarity	NPD5739	Approved
0.8037	Intermediate Similarity	NPD6675	Approved
0.7981	Intermediate Similarity	NPD5696	Approved
0.798	Intermediate Similarity	NPD5737	Approved
0.798	Intermediate Similarity	NPD6672	Approved
0.7963	Intermediate Similarity	NPD5697	Approved
0.7913	Intermediate Similarity	NPD6319	Approved
0.7909	Intermediate Similarity	NPD6883	Approved
0.7909	Intermediate Similarity	NPD7290	Approved
0.7909	Intermediate Similarity	NPD7102	Approved
0.79	Intermediate Similarity	NPD6904	Approved
0.79	Intermediate Similarity	NPD6080	Approved
0.79	Intermediate Similarity	NPD6673	Approved
0.789	Intermediate Similarity	NPD6011	Approved
0.7857	Intermediate Similarity	NPD4632	Approved
0.7838	Intermediate Similarity	NPD6869	Approved
0.7838	Intermediate Similarity	NPD6649	Approved
0.7838	Intermediate Similarity	NPD6617	Approved
0.7838	Intermediate Similarity	NPD6847	Approved
0.7838	Intermediate Similarity	NPD6650	Approved
0.7838	Intermediate Similarity	NPD8130	Phase 1
0.7818	Intermediate Similarity	NPD6372	Approved
0.7818	Intermediate Similarity	NPD6014	Approved
0.7818	Intermediate Similarity	NPD6013	Approved
0.7818	Intermediate Similarity	NPD6012	Approved
0.7818	Intermediate Similarity	NPD6373	Approved
0.7815	Intermediate Similarity	NPD7078	Approved
0.78	Intermediate Similarity	NPD6903	Approved
0.7798	Intermediate Similarity	NPD5701	Approved
0.7797	Intermediate Similarity	NPD7492	Approved
0.7768	Intermediate Similarity	NPD6882	Approved
0.7759	Intermediate Similarity	NPD6054	Approved
0.7745	Intermediate Similarity	NPD6050	Approved
0.7731	Intermediate Similarity	NPD6616	Approved
0.7723	Intermediate Similarity	NPD4753	Phase 2
0.7679	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5329	Approved
0.767	Intermediate Similarity	NPD6399	Phase 3
0.7652	Intermediate Similarity	NPD7115	Discovery
0.7647	Intermediate Similarity	NPD5692	Phase 3
0.7627	Intermediate Similarity	NPD6370	Approved
0.7607	Intermediate Similarity	NPD6059	Approved
0.7603	Intermediate Similarity	NPD7736	Approved
0.76	Intermediate Similarity	NPD6098	Approved
0.76	Intermediate Similarity	NPD5690	Phase 2
0.76	Intermediate Similarity	NPD7334	Approved
0.76	Intermediate Similarity	NPD7146	Approved
0.76	Intermediate Similarity	NPD7521	Approved
0.76	Intermediate Similarity	NPD6409	Approved
0.76	Intermediate Similarity	NPD6684	Approved
0.76	Intermediate Similarity	NPD5330	Approved
0.7589	Intermediate Similarity	NPD4634	Approved
0.7576	Intermediate Similarity	NPD4197	Approved
0.7573	Intermediate Similarity	NPD5693	Phase 1
0.7573	Intermediate Similarity	NPD5694	Approved
0.757	Intermediate Similarity	NPD5286	Approved
0.757	Intermediate Similarity	NPD4696	Approved
0.757	Intermediate Similarity	NPD5285	Approved
0.7547	Intermediate Similarity	NPD4755	Approved
0.7542	Intermediate Similarity	NPD6016	Approved
0.7542	Intermediate Similarity	NPD6015	Approved
0.7524	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5210	Approved
0.7524	Intermediate Similarity	NPD4629	Approved
0.7521	Intermediate Similarity	NPD8293	Discontinued
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD6009	Approved
0.7479	Intermediate Similarity	NPD5988	Approved
0.7453	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5222	Approved
0.7453	Intermediate Similarity	NPD5221	Approved
0.7451	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6335	Approved
0.7431	Intermediate Similarity	NPD5226	Approved
0.7431	Intermediate Similarity	NPD5211	Phase 2
0.7431	Intermediate Similarity	NPD5225	Approved
0.7431	Intermediate Similarity	NPD4633	Approved
0.7431	Intermediate Similarity	NPD5224	Approved
0.7426	Intermediate Similarity	NPD5280	Approved
0.7426	Intermediate Similarity	NPD4694	Approved
0.7417	Intermediate Similarity	NPD7604	Phase 2
0.7414	Intermediate Similarity	NPD6274	Approved
0.7407	Intermediate Similarity	NPD4700	Approved
0.7404	Intermediate Similarity	NPD5284	Approved
0.7404	Intermediate Similarity	NPD5281	Approved
0.7404	Intermediate Similarity	NPD6079	Approved
0.7395	Intermediate Similarity	NPD5983	Phase 2
0.7387	Intermediate Similarity	NPD6008	Approved
0.7383	Intermediate Similarity	NPD5173	Approved
0.7379	Intermediate Similarity	NPD5328	Approved
0.7374	Intermediate Similarity	NPD4221	Approved
0.7374	Intermediate Similarity	NPD4223	Phase 3
0.7373	Intermediate Similarity	NPD7101	Approved
0.7373	Intermediate Similarity	NPD7100	Approved
0.7364	Intermediate Similarity	NPD5175	Approved
0.7364	Intermediate Similarity	NPD5174	Approved
0.735	Intermediate Similarity	NPD6317	Approved
0.7308	Intermediate Similarity	NPD5207	Approved
0.7297	Intermediate Similarity	NPD5141	Approved
0.7295	Intermediate Similarity	NPD6336	Discontinued
0.729	Intermediate Similarity	NPD4697	Phase 3
0.7288	Intermediate Similarity	NPD6314	Approved
0.7288	Intermediate Similarity	NPD6313	Approved
0.7282	Intermediate Similarity	NPD5208	Approved
0.7265	Intermediate Similarity	NPD6868	Approved
0.7255	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5279	Phase 3
0.725	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD3133	Approved
0.7228	Intermediate Similarity	NPD3665	Phase 1
0.7228	Intermediate Similarity	NPD3666	Approved
0.7228	Intermediate Similarity	NPD4786	Approved
0.7207	Intermediate Similarity	NPD4754	Approved
0.7196	Intermediate Similarity	NPD5654	Approved
0.7177	Intermediate Similarity	NPD6033	Approved
0.7172	Intermediate Similarity	NPD4695	Discontinued
0.7168	Intermediate Similarity	NPD6412	Phase 2
0.7155	Intermediate Similarity	NPD6053	Discontinued
0.7107	Intermediate Similarity	NPD6908	Approved
0.7107	Intermediate Similarity	NPD6909	Approved
0.7105	Intermediate Similarity	NPD4730	Approved
0.7105	Intermediate Similarity	NPD5128	Approved
0.7105	Intermediate Similarity	NPD4729	Approved
0.7103	Intermediate Similarity	NPD7748	Approved
0.7103	Intermediate Similarity	NPD6001	Approved
0.7087	Intermediate Similarity	NPD4693	Phase 3
0.7087	Intermediate Similarity	NPD4689	Approved
0.7087	Intermediate Similarity	NPD4688	Approved
0.7087	Intermediate Similarity	NPD4138	Approved
0.7087	Intermediate Similarity	NPD5205	Approved
0.7087	Intermediate Similarity	NPD4690	Approved
0.708	Intermediate Similarity	NPD4768	Approved
0.708	Intermediate Similarity	NPD4767	Approved
0.7075	Intermediate Similarity	NPD6411	Approved
0.7064	Intermediate Similarity	NPD5959	Approved
0.7048	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3667	Approved
0.7019	Intermediate Similarity	NPD3573	Approved
0.7018	Intermediate Similarity	NPD6614	Approved
0.7018	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4202	Approved
0.7	Intermediate Similarity	NPD4225	Approved
0.6984	Remote Similarity	NPD7319	Approved
0.6983	Remote Similarity	NPD5169	Approved
0.6983	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5247	Approved
0.6983	Remote Similarity	NPD5248	Approved
0.6983	Remote Similarity	NPD5250	Approved
0.6983	Remote Similarity	NPD5135	Approved
0.6983	Remote Similarity	NPD5251	Approved
0.6983	Remote Similarity	NPD5249	Phase 3
0.6981	Remote Similarity	NPD5785	Approved
0.697	Remote Similarity	NPD3617	Approved
0.6961	Remote Similarity	NPD4788	Approved
0.6931	Remote Similarity	NPD5369	Approved
0.6923	Remote Similarity	NPD3618	Phase 1
0.6923	Remote Similarity	NPD5127	Approved
0.6923	Remote Similarity	NPD5215	Approved
0.6923	Remote Similarity	NPD5217	Approved
0.6923	Remote Similarity	NPD5216	Approved
0.6916	Remote Similarity	NPD7515	Phase 2
0.6909	Remote Similarity	NPD7902	Approved
0.6903	Remote Similarity	NPD6052	Approved
0.69	Remote Similarity	NPD4195	Approved
0.6887	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6101	Approved
0.6881	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7507	Approved
0.6863	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD8328	Phase 3
0.6852	Remote Similarity	NPD5133	Approved
0.6847	Remote Similarity	NPD7638	Approved
0.6838	Remote Similarity	NPD6371	Approved
0.6827	Remote Similarity	NPD5363	Approved
0.6814	Remote Similarity	NPD5091	Approved
0.681	Remote Similarity	NPD5168	Approved
0.6803	Remote Similarity	NPD4522	Approved
0.6797	Remote Similarity	NPD5956	Approved
0.6789	Remote Similarity	NPD5282	Discontinued
0.6786	Remote Similarity	NPD7640	Approved
0.6786	Remote Similarity	NPD7639	Approved
0.6762	Remote Similarity	NPD5786	Approved
0.675	Remote Similarity	NPD5167	Approved
0.6731	Remote Similarity	NPD3668	Phase 3
0.6699	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6435	Approved
0.6697	Remote Similarity	NPD5779	Approved
0.6697	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD4096	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