NPASS Compound

Structure

CID58052 OpenBabel06191715392D 35 39 0 0 1 0 0 0 0 0999 V2000 2.0517 3.3761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0004 3.1719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0967 -0.8941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4347 -1.6423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6673 -1.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3968 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5475 0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8488 1.4701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3963 -2.9416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -1.4711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -2.4517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8748 1.6885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2459 -1.4710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8488 -0.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4504 2.4812 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4248 2.3791 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6979 0.0008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5393 -2.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3968 -0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2456 -2.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 -0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8493 0.4904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6982 -0.9811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8488 0.4901 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2736 0.7936 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8236 1.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5475 -1.4715 0.0000 C 0 0 2 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 1.4368 -3.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1115 -2.9515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7979 1.3821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7464 -1.4648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2479 0.6915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 20 1 0 0 0 0 6 7 1 0 0 0 0 6 21 1 0 0 0 0 8 9 1 0 0 0 0 8 24 1 0 0 0 0 9 26 1 0 0 0 0 10 12 2 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 17 1 0 0 0 0 14 27 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 34 1 0 0 0 0 17 1 1 6 0 0 0 17 18 1 0 0 0 0 18 2 1 6 0 0 0 18 28 1 0 0 0 0 19 3 1 1 0 0 0 19 24 1 0 0 0 0 20 31 2 0 0 0 0 20 34 1 0 0 0 0 21 29 1 0 0 0 0 22 32 2 0 0 0 0 23 7 1 1 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 30 1 6 0 0 0 25 29 1 6 0 0 0 26 30 1 6 0 0 0 27 19 1 1 0 0 0 27 35 1 0 0 0 0 28 33 2 0 0 0 0 28 35 1 0 0 0 0 29 5 1 6 0 0 0 30 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.3
Volume:	515.423
LogP:	5.546
LogD:	4.748
LogS:	-5.122
# Rotatable Bonds:	5
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.381
Synthetic Accessibility Score:	5.162
Fsp3:	0.767
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.84
MDCK Permeability:	3.827669206657447e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.932
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	90.5897445678711%
Volume Distribution (VD):	1.421
Pgp-substrate:	3.0642406940460205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.373
CYP2C19-substrate:	0.585
CYP2C9-inhibitor:	0.199
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.144
CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.952
CYP3A4-substrate:	0.797

ADMET: Excretion

Clearance (CL):	5.936
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.612
Human Hepatotoxicity (H-HT):	0.375
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.358
Maximum Recommended Daily Dose:	0.756
Skin Sensitization:	0.961
Carcinogencity:	0.478
Eye Corrosion:	0.257
Eye Irritation:	0.281
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC58052

Natural Product ID:	NPC58052
*Common Name:**	Paraminabeolide B
IUPAC Name:	[(8R,9S,10R,13R,14S,17R)-17-[(1S)-1-[(2R,4S,5S)-4,5-dimethyl-6-oxooxan-2-yl]ethyl]-10-methyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-13-yl]methyl acetate
Synonyms:	Paraminabeolide B
Standard InCHIKey:	CJVKACGPAQCXAA-RXQWXACOSA-N
Standard InCHI:	InChI=1S/C30H42O5/c1-17-14-27(35-28(33)18(17)2)19(3)24-8-9-26-23-7-6-21-15-22(32)10-12-29(21,5)25(23)11-13-30(24,26)16-34-20(4)31/h10,12,15,17-19,23-27H,6-9,11,13-14,16H2,1-5H3/t17-,18-,19-,23+,24+,25-,26-,27+,29-,30-/m0/s1
SMILES:	CC(=O)OC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2[C@@H]([C@H]1C[C@H](C)[C@@H](C(=O)O1)C)C)CCC1=CC(=O)C=C[C@]31C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782223
PubChem CID:	53355240
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

*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
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	Eukaryota	n.a.	the western coast of Pingtung county, Taiwan, at a depth of 10 m	2009-MAY	PMID[21425785]
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21425785]
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	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
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	19300.0	nM	PMID[448514]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	14900.0	nM	PMID[448514]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	7.3	%	PMID[448514]

☑ 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 NPC58052 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	226
0.1-0.2	1311
0.2-0.3	5326
0.3-0.4	11199
0.4-0.5	9908
0.5-0.6	6263
0.6-0.7	5830
0.7-0.8	2495
0.8-0.85	126
0.85-0.9	10
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC111684
0.9551	High Similarity	NPC218301
0.8878	High Similarity	NPC164835
0.8878	High Similarity	NPC228669
0.8788	High Similarity	NPC96377
0.8763	High Similarity	NPC310981
0.8723	High Similarity	NPC304968
0.8723	High Similarity	NPC128488
0.8687	High Similarity	NPC255309
0.8632	High Similarity	NPC281134
0.8627	High Similarity	NPC197428
0.8617	High Similarity	NPC79117
0.8614	High Similarity	NPC470269
0.8586	High Similarity	NPC470954
0.8571	High Similarity	NPC195640
0.8557	High Similarity	NPC271387
0.8557	High Similarity	NPC114274
0.8557	High Similarity	NPC153792
0.8556	High Similarity	NPC109512
0.8539	High Similarity	NPC100297
0.8485	Intermediate Similarity	NPC271266
0.8485	Intermediate Similarity	NPC308351
0.8476	Intermediate Similarity	NPC471398
0.8462	Intermediate Similarity	NPC323765
0.8454	Intermediate Similarity	NPC292133
0.8454	Intermediate Similarity	NPC187159
0.8454	Intermediate Similarity	NPC108078
0.8404	Intermediate Similarity	NPC474842
0.8404	Intermediate Similarity	NPC475965
0.837	Intermediate Similarity	NPC264127
0.8365	Intermediate Similarity	NPC118860
0.8365	Intermediate Similarity	NPC231589
0.8365	Intermediate Similarity	NPC214797
0.8351	Intermediate Similarity	NPC42042
0.835	Intermediate Similarity	NPC258543
0.835	Intermediate Similarity	NPC241927
0.8333	Intermediate Similarity	NPC294266
0.8317	Intermediate Similarity	NPC235889
0.8316	Intermediate Similarity	NPC470230
0.8302	Intermediate Similarity	NPC470953
0.83	Intermediate Similarity	NPC22388
0.8298	Intermediate Similarity	NPC177141
0.8286	Intermediate Similarity	NPC170487
0.8283	Intermediate Similarity	NPC471041
0.8283	Intermediate Similarity	NPC218383
0.828	Intermediate Similarity	NPC30421
0.8265	Intermediate Similarity	NPC473456
0.8265	Intermediate Similarity	NPC23680
0.8265	Intermediate Similarity	NPC226986
0.8261	Intermediate Similarity	NPC29447
0.8261	Intermediate Similarity	NPC470223
0.8252	Intermediate Similarity	NPC61411
0.8247	Intermediate Similarity	NPC274417
0.8247	Intermediate Similarity	NPC33473
0.8235	Intermediate Similarity	NPC278628
0.8235	Intermediate Similarity	NPC181265
0.8235	Intermediate Similarity	NPC231530
0.8235	Intermediate Similarity	NPC470267
0.8235	Intermediate Similarity	NPC475571
0.8218	Intermediate Similarity	NPC95585
0.8218	Intermediate Similarity	NPC254202
0.8218	Intermediate Similarity	NPC282233
0.8218	Intermediate Similarity	NPC140723
0.8211	Intermediate Similarity	NPC273199
0.8211	Intermediate Similarity	NPC328141
0.82	Intermediate Similarity	NPC476240
0.82	Intermediate Similarity	NPC224720
0.82	Intermediate Similarity	NPC474327
0.82	Intermediate Similarity	NPC472924
0.82	Intermediate Similarity	NPC476223
0.8191	Intermediate Similarity	NPC97884
0.8191	Intermediate Similarity	NPC472220
0.8191	Intermediate Similarity	NPC28227
0.819	Intermediate Similarity	NPC470960
0.8182	Intermediate Similarity	NPC176845
0.8182	Intermediate Similarity	NPC471582
0.8173	Intermediate Similarity	NPC304495
0.8172	Intermediate Similarity	NPC471042
0.8165	Intermediate Similarity	NPC476960
0.8155	Intermediate Similarity	NPC475294
0.8152	Intermediate Similarity	NPC100391
0.8144	Intermediate Similarity	NPC56525
0.8144	Intermediate Similarity	NPC269729
0.8137	Intermediate Similarity	NPC189616
0.8132	Intermediate Similarity	NPC327969
0.8132	Intermediate Similarity	NPC321289
0.8131	Intermediate Similarity	NPC474181
0.8113	Intermediate Similarity	NPC71348
0.8105	Intermediate Similarity	NPC262043
0.8105	Intermediate Similarity	NPC471043
0.8105	Intermediate Similarity	NPC305039
0.8105	Intermediate Similarity	NPC474570
0.8105	Intermediate Similarity	NPC469546
0.8105	Intermediate Similarity	NPC186688
0.81	Intermediate Similarity	NPC83709
0.81	Intermediate Similarity	NPC104861
0.81	Intermediate Similarity	NPC167974
0.81	Intermediate Similarity	NPC476274
0.8091	Intermediate Similarity	NPC476962
0.8091	Intermediate Similarity	NPC476961
0.8085	Intermediate Similarity	NPC93778
0.8077	Intermediate Similarity	NPC94529
0.8073	Intermediate Similarity	NPC473720
0.8065	Intermediate Similarity	NPC2709
0.8061	Intermediate Similarity	NPC469599
0.8061	Intermediate Similarity	NPC470229
0.8061	Intermediate Similarity	NPC470016
0.8061	Intermediate Similarity	NPC317586
0.8058	Intermediate Similarity	NPC196528
0.8058	Intermediate Similarity	NPC470309
0.8056	Intermediate Similarity	NPC270958
0.8056	Intermediate Similarity	NPC190286
0.8056	Intermediate Similarity	NPC476963
0.8041	Intermediate Similarity	NPC206810
0.8041	Intermediate Similarity	NPC470923
0.8039	Intermediate Similarity	NPC275583
0.8039	Intermediate Similarity	NPC36321
0.8037	Intermediate Similarity	NPC255017
0.8021	Intermediate Similarity	NPC471896
0.8	Intermediate Similarity	NPC473203
0.8	Intermediate Similarity	NPC474242
0.8	Intermediate Similarity	NPC246205
0.8	Intermediate Similarity	NPC471475
0.8	Intermediate Similarity	NPC197386
0.8	Intermediate Similarity	NPC98868
0.8	Intermediate Similarity	NPC477854
0.8	Intermediate Similarity	NPC474793
0.8	Intermediate Similarity	NPC475520
0.8	Intermediate Similarity	NPC41405
0.7981	Intermediate Similarity	NPC476958
0.7981	Intermediate Similarity	NPC44063
0.798	Intermediate Similarity	NPC322063
0.798	Intermediate Similarity	NPC122324
0.798	Intermediate Similarity	NPC329910
0.798	Intermediate Similarity	NPC471775
0.798	Intermediate Similarity	NPC151725
0.798	Intermediate Similarity	NPC106425
0.798	Intermediate Similarity	NPC471039
0.798	Intermediate Similarity	NPC29410
0.798	Intermediate Similarity	NPC200054
0.798	Intermediate Similarity	NPC328371
0.7979	Intermediate Similarity	NPC220478
0.7978	Intermediate Similarity	NPC472300
0.7961	Intermediate Similarity	NPC29705
0.7961	Intermediate Similarity	NPC96268
0.7959	Intermediate Similarity	NPC473435
0.7959	Intermediate Similarity	NPC471078
0.7959	Intermediate Similarity	NPC471207
0.7959	Intermediate Similarity	NPC475118
0.7959	Intermediate Similarity	NPC473280
0.7959	Intermediate Similarity	NPC166906
0.7959	Intermediate Similarity	NPC184870
0.7959	Intermediate Similarity	NPC471040
0.7959	Intermediate Similarity	NPC473431
0.7957	Intermediate Similarity	NPC85774
0.7957	Intermediate Similarity	NPC320801
0.7957	Intermediate Similarity	NPC214043
0.7944	Intermediate Similarity	NPC236217
0.7944	Intermediate Similarity	NPC234042
0.7944	Intermediate Similarity	NPC152117
0.7941	Intermediate Similarity	NPC475320
0.7941	Intermediate Similarity	NPC473163
0.7941	Intermediate Similarity	NPC136289
0.7938	Intermediate Similarity	NPC476934
0.7938	Intermediate Similarity	NPC154101
0.7938	Intermediate Similarity	NPC221282
0.7938	Intermediate Similarity	NPC272746
0.7935	Intermediate Similarity	NPC240302
0.7935	Intermediate Similarity	NPC320514
0.7925	Intermediate Similarity	NPC37116
0.7925	Intermediate Similarity	NPC473627
0.7925	Intermediate Similarity	NPC5284
0.7921	Intermediate Similarity	NPC475385
0.7921	Intermediate Similarity	NPC471413
0.7921	Intermediate Similarity	NPC472972
0.7921	Intermediate Similarity	NPC475392
0.7921	Intermediate Similarity	NPC475202
0.7921	Intermediate Similarity	NPC241221
0.7921	Intermediate Similarity	NPC287833
0.7917	Intermediate Similarity	NPC477943
0.7917	Intermediate Similarity	NPC474679
0.7909	Intermediate Similarity	NPC118638
0.7909	Intermediate Similarity	NPC153440
0.7905	Intermediate Similarity	NPC275539
0.7905	Intermediate Similarity	NPC189075
0.79	Intermediate Similarity	NPC96839
0.79	Intermediate Similarity	NPC84335
0.79	Intermediate Similarity	NPC38530
0.7895	Intermediate Similarity	NPC167877
0.7895	Intermediate Similarity	NPC96496
0.7895	Intermediate Similarity	NPC136948
0.7895	Intermediate Similarity	NPC58063
0.789	Intermediate Similarity	NPC176840
0.789	Intermediate Similarity	NPC148458
0.7885	Intermediate Similarity	NPC469874
0.7879	Intermediate Similarity	NPC98639
0.7879	Intermediate Similarity	NPC174948
0.7879	Intermediate Similarity	NPC279974
0.7879	Intermediate Similarity	NPC470232
0.7879	Intermediate Similarity	NPC469995

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 NPC58052 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1527
0.2-0.3	4028
0.3-0.4	2230
0.4-0.5	682
0.5-0.6	181
0.6-0.7	151
0.7-0.8	149
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8587	High Similarity	NPD5737	Approved
0.8587	High Similarity	NPD6672	Approved
0.8587	High Similarity	NPD7513	Clinical (unspecified phase)
0.8571	High Similarity	NPD7521	Approved
0.8571	High Similarity	NPD6409	Approved
0.8571	High Similarity	NPD6684	Approved
0.8571	High Similarity	NPD5330	Approved
0.8571	High Similarity	NPD7334	Approved
0.8571	High Similarity	NPD7146	Approved
0.8387	Intermediate Similarity	NPD6903	Approved
0.828	Intermediate Similarity	NPD3573	Approved
0.8235	Intermediate Similarity	NPD6008	Approved
0.8125	Intermediate Similarity	NPD6079	Approved
0.8105	Intermediate Similarity	NPD6673	Approved
0.8105	Intermediate Similarity	NPD6904	Approved
0.8105	Intermediate Similarity	NPD6080	Approved
0.8077	Intermediate Similarity	NPD6899	Approved
0.8077	Intermediate Similarity	NPD6881	Approved
0.8041	Intermediate Similarity	NPD6399	Phase 3
0.7981	Intermediate Similarity	NPD5697	Approved
0.7925	Intermediate Similarity	NPD6883	Approved
0.7925	Intermediate Similarity	NPD7290	Approved
0.7925	Intermediate Similarity	NPD7102	Approved
0.7917	Intermediate Similarity	NPD5328	Approved
0.7905	Intermediate Similarity	NPD6011	Approved
0.79	Intermediate Similarity	NPD6083	Phase 2
0.79	Intermediate Similarity	NPD6084	Phase 2
0.7885	Intermediate Similarity	NPD6402	Approved
0.7885	Intermediate Similarity	NPD5739	Approved
0.7885	Intermediate Similarity	NPD7128	Approved
0.7885	Intermediate Similarity	NPD6675	Approved
0.7879	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD4632	Approved
0.785	Intermediate Similarity	NPD6869	Approved
0.785	Intermediate Similarity	NPD6617	Approved
0.785	Intermediate Similarity	NPD6649	Approved
0.785	Intermediate Similarity	NPD6650	Approved
0.785	Intermediate Similarity	NPD8130	Phase 1
0.785	Intermediate Similarity	NPD6847	Approved
0.783	Intermediate Similarity	NPD6013	Approved
0.783	Intermediate Similarity	NPD6012	Approved
0.783	Intermediate Similarity	NPD6014	Approved
0.7812	Intermediate Similarity	NPD5208	Approved
0.781	Intermediate Similarity	NPD6412	Phase 2
0.78	Intermediate Similarity	NPD5221	Approved
0.78	Intermediate Similarity	NPD5222	Approved
0.78	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD6098	Approved
0.7778	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7748	Approved
0.7778	Intermediate Similarity	NPD7900	Approved
0.7778	Intermediate Similarity	NPD6882	Approved
0.7778	Intermediate Similarity	NPD8297	Approved
0.7755	Intermediate Similarity	NPD6050	Approved
0.7755	Intermediate Similarity	NPD5694	Approved
0.7755	Intermediate Similarity	NPD5693	Phase 1
0.7736	Intermediate Similarity	NPD7320	Approved
0.7723	Intermediate Similarity	NPD5173	Approved
0.77	Intermediate Similarity	NPD5695	Phase 3
0.7664	Intermediate Similarity	NPD6372	Approved
0.7664	Intermediate Similarity	NPD6373	Approved
0.7658	Intermediate Similarity	NPD6009	Approved
0.7653	Intermediate Similarity	NPD5692	Phase 3
0.7653	Intermediate Similarity	NPD5207	Approved
0.7647	Intermediate Similarity	NPD5696	Approved
0.7647	Intermediate Similarity	NPD7638	Approved
0.7642	Intermediate Similarity	NPD5701	Approved
0.7611	Intermediate Similarity	NPD6319	Approved
0.7579	Intermediate Similarity	NPD3666	Approved
0.7579	Intermediate Similarity	NPD4786	Approved
0.7579	Intermediate Similarity	NPD3665	Phase 1
0.7579	Intermediate Similarity	NPD3133	Approved
0.7576	Intermediate Similarity	NPD7515	Phase 2
0.7573	Intermediate Similarity	NPD7640	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.7573	Intermediate Similarity	NPD5285	Approved
0.7573	Intermediate Similarity	NPD5286	Approved
0.7573	Intermediate Similarity	NPD4696	Approved
0.7568	Intermediate Similarity	NPD6868	Approved
0.7565	Intermediate Similarity	NPD7604	Phase 2
0.7553	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD7902	Approved
0.7544	Intermediate Similarity	NPD5983	Phase 2
0.7523	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.7458	Intermediate Similarity	NPD7736	Approved
0.7456	Intermediate Similarity	NPD6054	Approved
0.7451	Intermediate Similarity	NPD4697	Phase 3
0.7436	Intermediate Similarity	NPD6336	Discontinued
0.7436	Intermediate Similarity	NPD6616	Approved
0.7434	Intermediate Similarity	NPD6335	Approved
0.7429	Intermediate Similarity	NPD4633	Approved
0.7429	Intermediate Similarity	NPD5225	Approved
0.7429	Intermediate Similarity	NPD5224	Approved
0.7429	Intermediate Similarity	NPD5226	Approved
0.7429	Intermediate Similarity	NPD5211	Phase 2
0.7426	Intermediate Similarity	NPD6001	Approved
0.7423	Intermediate Similarity	NPD3618	Phase 1
0.74	Intermediate Similarity	NPD5281	Approved
0.74	Intermediate Similarity	NPD5284	Approved
0.7396	Intermediate Similarity	NPD3668	Phase 3
0.7379	Intermediate Similarity	NPD4755	Approved
0.7374	Intermediate Similarity	NPD4753	Phase 2
0.7373	Intermediate Similarity	NPD7078	Approved
0.7368	Intermediate Similarity	NPD4221	Approved
0.7368	Intermediate Similarity	NPD3667	Approved
0.7368	Intermediate Similarity	NPD7100	Approved
0.7368	Intermediate Similarity	NPD4223	Phase 3
0.7368	Intermediate Similarity	NPD7101	Approved
0.7358	Intermediate Similarity	NPD5175	Approved
0.7358	Intermediate Similarity	NPD5174	Approved
0.7353	Intermediate Similarity	NPD4629	Approved
0.7353	Intermediate Similarity	NPD5210	Approved
0.7345	Intermediate Similarity	NPD7115	Discovery
0.7345	Intermediate Similarity	NPD6317	Approved
0.7328	Intermediate Similarity	NPD6370	Approved
0.732	Intermediate Similarity	NPD1694	Approved
0.732	Intermediate Similarity	NPD5329	Approved
0.7315	Intermediate Similarity	NPD6614	Approved
0.7303	Intermediate Similarity	NPD4747	Approved
0.7303	Intermediate Similarity	NPD4691	Approved
0.729	Intermediate Similarity	NPD5141	Approved
0.7282	Intermediate Similarity	NPD7732	Phase 3
0.7281	Intermediate Similarity	NPD6314	Approved
0.7281	Intermediate Similarity	NPD6313	Approved
0.7273	Intermediate Similarity	NPD4634	Approved
0.7257	Intermediate Similarity	NPD6274	Approved
0.7253	Intermediate Similarity	NPD4058	Approved
0.7248	Intermediate Similarity	NPD6686	Approved
0.7245	Intermediate Similarity	NPD5279	Phase 3
0.7245	Intermediate Similarity	NPD5690	Phase 2
0.7241	Intermediate Similarity	NPD6016	Approved
0.7241	Intermediate Similarity	NPD6015	Approved
0.7238	Intermediate Similarity	NPD4700	Approved
0.7228	Intermediate Similarity	NPD8034	Phase 2
0.7228	Intermediate Similarity	NPD6411	Approved
0.7228	Intermediate Similarity	NPD8035	Phase 2
0.7216	Intermediate Similarity	NPD4197	Approved
0.72	Intermediate Similarity	NPD6051	Approved
0.7196	Intermediate Similarity	NPD6052	Approved
0.7191	Intermediate Similarity	NPD4137	Phase 3
0.7184	Intermediate Similarity	NPD5654	Approved
0.7179	Intermediate Similarity	NPD5988	Approved
0.7157	Intermediate Similarity	NPD4202	Approved
0.7155	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5168	Approved
0.7091	Intermediate Similarity	NPD4729	Approved
0.7091	Intermediate Similarity	NPD4730	Approved
0.7083	Intermediate Similarity	NPD8293	Discontinued
0.708	Intermediate Similarity	NPD6858	Approved
0.708	Intermediate Similarity	NPD7094	Approved
0.7071	Intermediate Similarity	NPD4688	Approved
0.7071	Intermediate Similarity	NPD4693	Phase 3
0.7071	Intermediate Similarity	NPD4689	Approved
0.7071	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4690	Approved
0.7071	Intermediate Similarity	NPD5205	Approved
0.7071	Intermediate Similarity	NPD4138	Approved
0.7065	Intermediate Similarity	NPD4687	Approved
0.7065	Intermediate Similarity	NPD5733	Approved
0.7053	Intermediate Similarity	NPD4195	Approved
0.7048	Intermediate Similarity	NPD5959	Approved
0.7037	Intermediate Similarity	NPD4754	Approved
0.703	Intermediate Similarity	NPD6101	Approved
0.703	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4695	Discontinued
0.6975	Remote Similarity	NPD8328	Phase 3
0.6967	Remote Similarity	NPD7319	Approved
0.6964	Remote Similarity	NPD5247	Approved
0.6964	Remote Similarity	NPD5135	Approved
0.6964	Remote Similarity	NPD5248	Approved
0.6964	Remote Similarity	NPD5169	Approved
0.6964	Remote Similarity	NPD5250	Approved
0.6964	Remote Similarity	NPD5249	Phase 3
0.6964	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5251	Approved
0.6952	Remote Similarity	NPD7614	Phase 1
0.6949	Remote Similarity	NPD6908	Approved
0.6949	Remote Similarity	NPD6909	Approved
0.6947	Remote Similarity	NPD3617	Approved
0.6944	Remote Similarity	NPD7632	Discontinued
0.6939	Remote Similarity	NPD4788	Approved
0.6937	Remote Similarity	NPD5128	Approved
0.6909	Remote Similarity	NPD4767	Approved
0.6909	Remote Similarity	NPD4768	Approved
0.6903	Remote Similarity	NPD5217	Approved
0.6903	Remote Similarity	NPD5216	Approved
0.6903	Remote Similarity	NPD5127	Approved
0.6903	Remote Similarity	NPD5215	Approved
0.69	Remote Similarity	NPD5280	Approved
0.69	Remote Similarity	NPD4694	Approved
0.6893	Remote Similarity	NPD7637	Suspended
0.6855	Remote Similarity	NPD7260	Phase 2
0.6848	Remote Similarity	NPD5276	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