NPASS Compound

Structure

CID38232 OpenBabel06191715372D 36 39 0 0 1 0 0 0 0 0999 V2000 0.2735 -3.2322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4659 -5.9083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -2.4790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7339 1.6011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3867 2.9672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2638 2.4607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5397 -0.5250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2160 -3.4358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8185 -2.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6422 -4.2261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8470 1.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6938 1.9546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6923 -0.9765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2320 0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6920 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3859 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6930 -0.9774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8473 -2.4420 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0397 -5.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8462 -1.4660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8045 1.2994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8470 -1.4655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8468 0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6932 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5403 1.4656 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2323 1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9770 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0109 -5.2199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3864 1.9541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5400 0.4880 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 -5.6011 0.3438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4084 -6.1119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5847 -4.4297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0786 1.9534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 21 2 0 0 0 0 4 22 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 13 1 0 0 0 0 12 24 2 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 32 1 0 0 0 0 17 31 1 0 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 19 1 1 1 0 0 0 20 29 1 0 0 0 0 21 28 1 0 0 0 0 22 33 2 0 0 0 0 22 36 1 0 0 0 0 23 19 1 6 0 0 0 23 28 1 0 0 0 0 24 25 1 0 0 0 0 24 32 1 0 0 0 0 25 31 1 6 0 0 0 26 30 1 0 0 0 0 26 31 1 6 0 0 0 27 30 1 0 0 0 0 27 36 1 1 0 0 0 28 32 1 0 0 0 0 29 34 2 0 0 0 0 29 35 1 0 0 0 0 31 7 1 6 0 0 0 32 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.36
Volume:	549.781
LogP:	6.402
LogD:	5.304
LogS:	-5.535
# Rotatable Bonds:	7
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.304
Synthetic Accessibility Score:	5.257
Fsp3:	0.75
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:	-5.099
MDCK Permeability:	1.6057378161349334e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.778
30% Bioavailability (F30%):	0.091

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	100.27654266357422%
Volume Distribution (VD):	0.944
Pgp-substrate:	3.0895049571990967%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.239
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.329
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	2.061
Half-life (T1/2):	0.124

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.449
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.789
Skin Sensitization:	0.042
Carcinogencity:	0.033
Eye Corrosion:	0.004
Eye Irritation:	0.078
Respiratory Toxicity:	0.653

Download Data

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

Natural Product: NPC38232

Natural Product ID:	NPC38232
*Common Name:**	Ananosic Acid B
IUPAC Name:	(Z,6R)-6-[(3R,5R,9R,10R,14R,17R)-3-acetyloxy-4,4,10,14-tetramethyl-12-methylidene-2,3,5,6,9,11,13,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoic acid
Synonyms:	Ananosic acid B
Standard InCHIKey:	BBMSARKIPIKXRC-MSQCISNYSA-N
Standard InCHI:	InChI=1S/C32H48O4/c1-19(10-9-11-20(2)29(34)35)23-14-16-32(8)24-12-13-26-30(5,6)27(36-22(4)33)15-17-31(26,7)25(24)18-21(3)28(23)32/h11-12,19,23,25-28H,3,9-10,13-18H2,1-2,4-8H3,(H,34,35)/b20-11-/t19-,23-,25+,26+,27-,28?,31-,32+/m1/s1
SMILES:	C[C@H](CC/C=C(/C)C(=O)O)[C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](CC[C@]4(C)[C@H]3CC(=C)C12)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481073
PubChem CID:	44559519
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
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165154]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[20025236]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	seed	n.a.	PMID[21381710]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27599	Kadsura ananosma	Species	Schisandraceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	49.6	ug.mL-1	PMID[509161]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	0.54	ug.mL-1	PMID[509161]

☑ 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 NPC38232 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	163
0.1-0.2	1046
0.2-0.3	4305
0.3-0.4	12320
0.4-0.5	9855
0.5-0.6	6220
0.6-0.7	5573
0.7-0.8	2843
0.8-0.85	281
0.85-0.9	66
0.9-0.95	22
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9425	High Similarity	NPC472240
0.9425	High Similarity	NPC262858
0.9341	High Similarity	NPC141401
0.9205	High Similarity	NPC146554
0.9111	High Similarity	NPC476304
0.9111	High Similarity	NPC214697
0.9011	High Similarity	NPC279410
0.9011	High Similarity	NPC476186
0.9011	High Similarity	NPC119562
0.9	High Similarity	NPC212948
0.9	High Similarity	NPC74296
0.9	High Similarity	NPC110923
0.8889	High Similarity	NPC471896
0.8864	High Similarity	NPC474970
0.8854	High Similarity	NPC85742
0.8837	High Similarity	NPC256112
0.8817	High Similarity	NPC114743
0.8817	High Similarity	NPC276103
0.8817	High Similarity	NPC190713
0.8817	High Similarity	NPC195366
0.8817	High Similarity	NPC54248
0.8804	High Similarity	NPC474922
0.8791	High Similarity	NPC177641
0.8736	High Similarity	NPC476927
0.8723	High Similarity	NPC99726
0.8723	High Similarity	NPC253826
0.8721	High Similarity	NPC170303
0.8681	High Similarity	NPC175628
0.8681	High Similarity	NPC148414
0.8681	High Similarity	NPC111585
0.866	High Similarity	NPC180204
0.8632	High Similarity	NPC218107
0.8632	High Similarity	NPC92275
0.8587	High Similarity	NPC329842
0.8587	High Similarity	NPC470113
0.8587	High Similarity	NPC26888
0.8571	High Similarity	NPC177141
0.8571	High Similarity	NPC474889
0.8557	High Similarity	NPC136289
0.8542	High Similarity	NPC476274
0.8542	High Similarity	NPC266955
0.8542	High Similarity	NPC201406
0.8542	High Similarity	NPC251680
0.8511	High Similarity	NPC474909
0.8478	Intermediate Similarity	NPC78973
0.8469	Intermediate Similarity	NPC72151
0.8469	Intermediate Similarity	NPC297617
0.8469	Intermediate Similarity	NPC112009
0.8454	Intermediate Similarity	NPC476223
0.8454	Intermediate Similarity	NPC99411
0.8454	Intermediate Similarity	NPC224720
0.8454	Intermediate Similarity	NPC118174
0.8454	Intermediate Similarity	NPC81530
0.8454	Intermediate Similarity	NPC476240
0.8454	Intermediate Similarity	NPC115899
0.8444	Intermediate Similarity	NPC168231
0.8438	Intermediate Similarity	NPC478056
0.8427	Intermediate Similarity	NPC306951
0.8421	Intermediate Similarity	NPC88009
0.8421	Intermediate Similarity	NPC250757
0.8421	Intermediate Similarity	NPC472941
0.8421	Intermediate Similarity	NPC301534
0.8421	Intermediate Similarity	NPC456
0.8421	Intermediate Similarity	NPC7124
0.8409	Intermediate Similarity	NPC2524
0.8404	Intermediate Similarity	NPC201725
0.8404	Intermediate Similarity	NPC469406
0.8404	Intermediate Similarity	NPC159410
0.8391	Intermediate Similarity	NPC281880
0.8387	Intermediate Similarity	NPC473998
0.8387	Intermediate Similarity	NPC234335
0.837	Intermediate Similarity	NPC474704
0.837	Intermediate Similarity	NPC473999
0.837	Intermediate Similarity	NPC314727
0.837	Intermediate Similarity	NPC309603
0.837	Intermediate Similarity	NPC475921
0.8367	Intermediate Similarity	NPC320447
0.8367	Intermediate Similarity	NPC293753
0.8352	Intermediate Similarity	NPC142361
0.8352	Intermediate Similarity	NPC474684
0.8351	Intermediate Similarity	NPC473510
0.8351	Intermediate Similarity	NPC230546
0.8351	Intermediate Similarity	NPC471041
0.8333	Intermediate Similarity	NPC474013
0.8333	Intermediate Similarity	NPC320306
0.8333	Intermediate Similarity	NPC109528
0.8333	Intermediate Similarity	NPC210337
0.8333	Intermediate Similarity	NPC108078
0.8316	Intermediate Similarity	NPC84383
0.8316	Intermediate Similarity	NPC279974
0.8316	Intermediate Similarity	NPC476174
0.8316	Intermediate Similarity	NPC293052
0.8315	Intermediate Similarity	NPC79945
0.8315	Intermediate Similarity	NPC139206
0.8298	Intermediate Similarity	NPC27918
0.8298	Intermediate Similarity	NPC470224
0.8298	Intermediate Similarity	NPC472871
0.8295	Intermediate Similarity	NPC159148
0.8283	Intermediate Similarity	NPC476237
0.8283	Intermediate Similarity	NPC473523
0.828	Intermediate Similarity	NPC280149
0.828	Intermediate Similarity	NPC302280
0.828	Intermediate Similarity	NPC48010
0.828	Intermediate Similarity	NPC469400
0.828	Intermediate Similarity	NPC477149
0.828	Intermediate Similarity	NPC477147
0.828	Intermediate Similarity	NPC273199
0.828	Intermediate Similarity	NPC221111
0.8276	Intermediate Similarity	NPC153987
0.8276	Intermediate Similarity	NPC44083
0.8276	Intermediate Similarity	NPC30986
0.8276	Intermediate Similarity	NPC209430
0.8265	Intermediate Similarity	NPC473160
0.8265	Intermediate Similarity	NPC295110
0.8265	Intermediate Similarity	NPC25177
0.8265	Intermediate Similarity	NPC268829
0.8265	Intermediate Similarity	NPC222875
0.8265	Intermediate Similarity	NPC247701
0.8261	Intermediate Similarity	NPC104560
0.8261	Intermediate Similarity	NPC472870
0.8247	Intermediate Similarity	NPC108368
0.8247	Intermediate Similarity	NPC57079
0.8247	Intermediate Similarity	NPC98868
0.8242	Intermediate Similarity	NPC131813
0.8242	Intermediate Similarity	NPC325594
0.8242	Intermediate Similarity	NPC475069
0.8242	Intermediate Similarity	NPC175145
0.8229	Intermediate Similarity	NPC327788
0.8229	Intermediate Similarity	NPC253115
0.8229	Intermediate Similarity	NPC328371
0.8229	Intermediate Similarity	NPC304899
0.8222	Intermediate Similarity	NPC472265
0.8222	Intermediate Similarity	NPC33913
0.8222	Intermediate Similarity	NPC164577
0.8222	Intermediate Similarity	NPC474047
0.8218	Intermediate Similarity	NPC475294
0.8211	Intermediate Similarity	NPC57117
0.8211	Intermediate Similarity	NPC74751
0.8211	Intermediate Similarity	NPC8993
0.8211	Intermediate Similarity	NPC184870
0.8202	Intermediate Similarity	NPC101462
0.8202	Intermediate Similarity	NPC470049
0.82	Intermediate Similarity	NPC473543
0.8191	Intermediate Similarity	NPC474018
0.8191	Intermediate Similarity	NPC72845
0.8191	Intermediate Similarity	NPC475806
0.8191	Intermediate Similarity	NPC473986
0.8191	Intermediate Similarity	NPC189520
0.8182	Intermediate Similarity	NPC475344
0.8182	Intermediate Similarity	NPC273668
0.8182	Intermediate Similarity	NPC234892
0.8182	Intermediate Similarity	NPC206735
0.8182	Intermediate Similarity	NPC114540
0.8182	Intermediate Similarity	NPC281702
0.8182	Intermediate Similarity	NPC155332
0.8182	Intermediate Similarity	NPC283343
0.8182	Intermediate Similarity	NPC32577
0.8182	Intermediate Similarity	NPC22388
0.8182	Intermediate Similarity	NPC258547
0.8182	Intermediate Similarity	NPC476471
0.8173	Intermediate Similarity	NPC264634
0.8172	Intermediate Similarity	NPC474396
0.8172	Intermediate Similarity	NPC66344
0.8172	Intermediate Similarity	NPC473647
0.8172	Intermediate Similarity	NPC474570
0.8172	Intermediate Similarity	NPC16265
0.8172	Intermediate Similarity	NPC214387
0.8172	Intermediate Similarity	NPC262043
0.8172	Intermediate Similarity	NPC50488
0.8172	Intermediate Similarity	NPC170633
0.8163	Intermediate Similarity	NPC287833
0.8163	Intermediate Similarity	NPC241221
0.8163	Intermediate Similarity	NPC470074
0.8163	Intermediate Similarity	NPC307954
0.8163	Intermediate Similarity	NPC327431
0.8163	Intermediate Similarity	NPC476303
0.8155	Intermediate Similarity	NPC16270
0.8152	Intermediate Similarity	NPC475772
0.8152	Intermediate Similarity	NPC136948
0.8152	Intermediate Similarity	NPC166857
0.8152	Intermediate Similarity	NPC89747
0.8152	Intermediate Similarity	NPC159046
0.8152	Intermediate Similarity	NPC478104
0.8152	Intermediate Similarity	NPC187376
0.8152	Intermediate Similarity	NPC233836
0.8144	Intermediate Similarity	NPC475894
0.8144	Intermediate Similarity	NPC231751
0.8137	Intermediate Similarity	NPC472219
0.8137	Intermediate Similarity	NPC472217
0.8137	Intermediate Similarity	NPC472218
0.8137	Intermediate Similarity	NPC88701
0.8132	Intermediate Similarity	NPC266511
0.8132	Intermediate Similarity	NPC191965
0.8125	Intermediate Similarity	NPC174948
0.8125	Intermediate Similarity	NPC317586
0.8125	Intermediate Similarity	NPC69548
0.8125	Intermediate Similarity	NPC281134
0.8125	Intermediate Similarity	NPC470016
0.8125	Intermediate Similarity	NPC173875
0.8125	Intermediate Similarity	NPC184848

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 NPC38232 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	1264
0.2-0.3	3925
0.3-0.4	2624
0.4-0.5	695
0.5-0.6	188
0.6-0.7	174
0.7-0.8	132
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8542	High Similarity	NPD7640	Approved
0.8542	High Similarity	NPD7639	Approved
0.8438	Intermediate Similarity	NPD7638	Approved
0.8211	Intermediate Similarity	NPD7748	Approved
0.8105	Intermediate Similarity	NPD6399	Phase 3
0.8	Intermediate Similarity	NPD6079	Approved
0.7979	Intermediate Similarity	NPD5328	Approved
0.7961	Intermediate Similarity	NPD6899	Approved
0.7961	Intermediate Similarity	NPD6881	Approved
0.7959	Intermediate Similarity	NPD7902	Approved
0.7941	Intermediate Similarity	NPD6675	Approved
0.7941	Intermediate Similarity	NPD6402	Approved
0.7941	Intermediate Similarity	NPD7128	Approved
0.7941	Intermediate Similarity	NPD5739	Approved
0.7905	Intermediate Similarity	NPD8130	Phase 1
0.7879	Intermediate Similarity	NPD4225	Approved
0.7872	Intermediate Similarity	NPD6672	Approved
0.7872	Intermediate Similarity	NPD5737	Approved
0.787	Intermediate Similarity	NPD7115	Discovery
0.7864	Intermediate Similarity	NPD5697	Approved
0.7849	Intermediate Similarity	NPD6684	Approved
0.7849	Intermediate Similarity	NPD7146	Approved
0.7849	Intermediate Similarity	NPD7334	Approved
0.7849	Intermediate Similarity	NPD6409	Approved
0.7849	Intermediate Similarity	NPD5330	Approved
0.7849	Intermediate Similarity	NPD7521	Approved
0.7849	Intermediate Similarity	NPD3618	Phase 1
0.783	Intermediate Similarity	NPD8297	Approved
0.7822	Intermediate Similarity	NPD7632	Discontinued
0.7812	Intermediate Similarity	NPD7515	Phase 2
0.7812	Intermediate Similarity	NPD8034	Phase 2
0.7812	Intermediate Similarity	NPD8035	Phase 2
0.781	Intermediate Similarity	NPD7102	Approved
0.781	Intermediate Similarity	NPD6883	Approved
0.781	Intermediate Similarity	NPD7290	Approved
0.7789	Intermediate Similarity	NPD6051	Approved
0.7788	Intermediate Similarity	NPD6011	Approved
0.7788	Intermediate Similarity	NPD7320	Approved
0.7778	Intermediate Similarity	NPD6083	Phase 2
0.7778	Intermediate Similarity	NPD6084	Phase 2
0.7778	Intermediate Similarity	NPD7525	Registered
0.7736	Intermediate Similarity	NPD6649	Approved
0.7736	Intermediate Similarity	NPD6847	Approved
0.7736	Intermediate Similarity	NPD6650	Approved
0.7736	Intermediate Similarity	NPD6617	Approved
0.7736	Intermediate Similarity	NPD6869	Approved
0.7714	Intermediate Similarity	NPD6012	Approved
0.7714	Intermediate Similarity	NPD6014	Approved
0.7714	Intermediate Similarity	NPD6013	Approved
0.7714	Intermediate Similarity	NPD6373	Approved
0.7714	Intermediate Similarity	NPD6372	Approved
0.7692	Intermediate Similarity	NPD5701	Approved
0.7684	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6903	Approved
0.7677	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5222	Approved
0.7677	Intermediate Similarity	NPD5221	Approved
0.7664	Intermediate Similarity	NPD6882	Approved
0.7653	Intermediate Similarity	NPD7900	Approved
0.7653	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5211	Phase 2
0.7634	Intermediate Similarity	NPD4786	Approved
0.7614	Intermediate Similarity	NPD7339	Approved
0.7614	Intermediate Similarity	NPD6942	Approved
0.76	Intermediate Similarity	NPD5173	Approved
0.7576	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5695	Phase 3
0.757	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4202	Approved
0.7525	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD5141	Approved
0.7473	Intermediate Similarity	NPD4195	Approved
0.7455	Intermediate Similarity	NPD6868	Approved
0.7451	Intermediate Similarity	NPD4696	Approved
0.7451	Intermediate Similarity	NPD5285	Approved
0.7451	Intermediate Similarity	NPD5286	Approved
0.7449	Intermediate Similarity	NPD7637	Suspended
0.7447	Intermediate Similarity	NPD3665	Phase 1
0.7447	Intermediate Similarity	NPD3666	Approved
0.7447	Intermediate Similarity	NPD3133	Approved
0.7426	Intermediate Similarity	NPD4755	Approved
0.7423	Intermediate Similarity	NPD6904	Approved
0.7423	Intermediate Similarity	NPD6673	Approved
0.7423	Intermediate Similarity	NPD6080	Approved
0.7419	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3667	Approved
0.7379	Intermediate Similarity	NPD5223	Approved
0.7333	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6335	Approved
0.7308	Intermediate Similarity	NPD5225	Approved
0.7308	Intermediate Similarity	NPD4633	Approved
0.7308	Intermediate Similarity	NPD5226	Approved
0.7308	Intermediate Similarity	NPD5224	Approved
0.7297	Intermediate Similarity	NPD6274	Approved
0.7292	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7645	Phase 2
0.7282	Intermediate Similarity	NPD4700	Approved
0.7273	Intermediate Similarity	NPD5693	Phase 1
0.7273	Intermediate Similarity	NPD4632	Approved
0.7264	Intermediate Similarity	NPD6008	Approved
0.7257	Intermediate Similarity	NPD7100	Approved
0.7257	Intermediate Similarity	NPD7101	Approved
0.7245	Intermediate Similarity	NPD4753	Phase 2
0.7238	Intermediate Similarity	NPD5174	Approved
0.7238	Intermediate Similarity	NPD5175	Approved
0.7234	Intermediate Similarity	NPD4221	Approved
0.7234	Intermediate Similarity	NPD4223	Phase 3
0.7232	Intermediate Similarity	NPD6317	Approved
0.7216	Intermediate Similarity	NPD3573	Approved
0.7216	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8294	Approved
0.7193	Intermediate Similarity	NPD8377	Approved
0.7188	Intermediate Similarity	NPD1694	Approved
0.7188	Intermediate Similarity	NPD5329	Approved
0.7168	Intermediate Similarity	NPD7327	Approved
0.7168	Intermediate Similarity	NPD6313	Approved
0.7168	Intermediate Similarity	NPD6314	Approved
0.7168	Intermediate Similarity	NPD7328	Approved
0.7158	Intermediate Similarity	NPD6695	Phase 3
0.7143	Intermediate Similarity	NPD5208	Approved
0.713	Intermediate Similarity	NPD7503	Approved
0.713	Intermediate Similarity	NPD8380	Approved
0.713	Intermediate Similarity	NPD8379	Approved
0.713	Intermediate Similarity	NPD8335	Approved
0.713	Intermediate Similarity	NPD8378	Approved
0.713	Intermediate Similarity	NPD8296	Approved
0.713	Intermediate Similarity	NPD8033	Approved
0.7129	Intermediate Similarity	NPD6001	Approved
0.7115	Intermediate Similarity	NPD6404	Discontinued
0.7113	Intermediate Similarity	NPD6098	Approved
0.7113	Intermediate Similarity	NPD5279	Phase 3
0.7105	Intermediate Similarity	NPD7516	Approved
0.71	Intermediate Similarity	NPD6050	Approved
0.71	Intermediate Similarity	NPD5281	Approved
0.71	Intermediate Similarity	NPD5284	Approved
0.7083	Intermediate Similarity	NPD3668	Phase 3
0.7083	Intermediate Similarity	NPD4197	Approved
0.7083	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6009	Approved
0.7079	Intermediate Similarity	NPD4243	Approved
0.7075	Intermediate Similarity	NPD4754	Approved
0.7059	Intermediate Similarity	NPD5210	Approved
0.7059	Intermediate Similarity	NPD4629	Approved
0.7043	Intermediate Similarity	NPD6319	Approved
0.7041	Intermediate Similarity	NPD7750	Discontinued
0.7019	Intermediate Similarity	NPD5290	Discontinued
0.7009	Intermediate Similarity	NPD7604	Phase 2
0.7	Intermediate Similarity	NPD5692	Phase 3
0.6989	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6908	Approved
0.6983	Remote Similarity	NPD6909	Approved
0.6983	Remote Similarity	NPD5983	Phase 2
0.6983	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4729	Approved
0.6972	Remote Similarity	NPD6686	Approved
0.6972	Remote Similarity	NPD4730	Approved
0.6972	Remote Similarity	NPD5168	Approved
0.6972	Remote Similarity	NPD5128	Approved
0.6957	Remote Similarity	NPD6117	Approved
0.6949	Remote Similarity	NPD7492	Approved
0.6944	Remote Similarity	NPD4767	Approved
0.6944	Remote Similarity	NPD4768	Approved
0.6939	Remote Similarity	NPD4138	Approved
0.6939	Remote Similarity	NPD4693	Phase 3
0.6939	Remote Similarity	NPD5205	Approved
0.6939	Remote Similarity	NPD4623	Approved
0.6939	Remote Similarity	NPD4689	Approved
0.6939	Remote Similarity	NPD4688	Approved
0.6939	Remote Similarity	NPD5690	Phase 2
0.6939	Remote Similarity	NPD4519	Discontinued
0.6939	Remote Similarity	NPD4690	Approved
0.6931	Remote Similarity	NPD5694	Approved
0.6923	Remote Similarity	NPD4785	Approved
0.6923	Remote Similarity	NPD4784	Approved
0.6923	Remote Similarity	NPD6926	Approved
0.6923	Remote Similarity	NPD6924	Approved
0.6917	Remote Similarity	NPD7736	Approved
0.6915	Remote Similarity	NPD6929	Approved
0.6909	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6054	Approved
0.6891	Remote Similarity	NPD6336	Discontinued
0.6891	Remote Similarity	NPD7507	Approved
0.6891	Remote Similarity	NPD6616	Approved
0.6882	Remote Similarity	NPD6116	Phase 1
0.6881	Remote Similarity	NPD6412	Phase 2
0.6869	Remote Similarity	NPD7524	Approved
0.6848	Remote Similarity	NPD8264	Approved
0.6847	Remote Similarity	NPD5248	Approved
0.6847	Remote Similarity	NPD5247	Approved
0.6847	Remote Similarity	NPD5135	Approved
0.6847	Remote Similarity	NPD5169	Approved
0.6847	Remote Similarity	NPD4634	Approved
0.6847	Remote Similarity	NPD5249	Phase 3
0.6847	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5251	Approved
0.6847	Remote Similarity	NPD5250	Approved
0.6847	Remote Similarity	NPD5955	Clinical (unspecified phase)

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