NPASS Compound

Structure

NPC31985 OpenBabel07101719522D 31 34 0 0 1 0 0 0 0 0999 V2000 2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 4.1622 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 -3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 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 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9000 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 -3.4641 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2308 4.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 17 1 0 0 0 0 5 26 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 27 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 26 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 25 1 0 0 0 0 15 28 1 0 0 0 0 16 1 1 1 0 0 0 16 18 1 0 0 0 0 17 29 2 0 0 0 0 18 26 1 1 0 0 0 19 20 1 0 0 0 0 19 24 1 1 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 21 30 2 0 0 0 0 22 25 1 1 0 0 0 22 31 1 0 0 0 0 23 24 1 6 0 0 0 23 27 1 0 0 0 0 24 3 1 1 0 0 0 25 4 1 6 0 0 0 26 27 1 1 0 0 0 27 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.31
Volume:	468.574
LogP:	3.643
LogD:	3.666
LogS:	-3.902
# Rotatable Bonds:	4
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	4.935
Fsp3:	0.852
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:	-5.017
MDCK Permeability:	1.6080755813163705e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.093
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.697
Plasma Protein Binding (PPB):	90.29544830322266%
Volume Distribution (VD):	0.6
Pgp-substrate:	7.359422206878662%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.799
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.821
CYP3A4-substrate:	0.889

ADMET: Excretion

Clearance (CL):	9.165
Half-life (T1/2):	0.168

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.351
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.546
Maximum Recommended Daily Dose:	0.727
Skin Sensitization:	0.235
Carcinogencity:	0.375
Eye Corrosion:	0.01
Eye Irritation:	0.016
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC31985

Natural Product ID:	NPC31985
*Common Name:**	Balsaminol D
IUPAC Name:	(3S,4S,8R,9S,10S,13R,14S,17R)-3-hydroxy-4-(hydroxymethyl)-4,9,13,14-tetramethyl-17-[(2R)-4-oxopentan-2-yl]-1,2,3,8,10,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-7-one
Synonyms:	Balsaminol D
Standard InCHIKey:	NBZHVWXCQLFQNW-ATYSFEEYSA-N
Standard InCHI:	InChI=1S/C27H42O4/c1-16(13-17(2)29)18-9-10-27(6)23-21(30)14-20-19(7-8-22(31)25(20,4)15-28)24(23,3)11-12-26(18,27)5/h14,16,18-19,22-23,28,31H,7-13,15H2,1-6H3/t16-,18-,19-,22+,23-,24+,25-,26-,27+/m1/s1
SMILES:	C[C@H](CC(=O)C)[C@H]1CC[C@@]2(C)[C@@H]3C(=O)C=C4[C@@H](CC[C@@H]([C@]4(C)CO)O)[C@]3(C)CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1254848
PubChem CID:	52947048
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	African	n.a.	PMID[19795842]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20541427]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31339732]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	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	5
Others	10

Activity Type	# Activity
Cell Line	1
Individual Protein	8
NON-MOLECULAR	2
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	133300.0	nM	PMID[468325]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	45600.0	nM	PMID[468325]
NPT2	Others	Unspecified		Selectivity Index	>	5.1	n.a.	PMID[468325]
NPT2	Others	Unspecified		Selectivity Index	>	2.9	n.a.	PMID[468325]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	25900.0	nM	PMID[468325]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	67100.0	nM	PMID[468326]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	27800.0	nM	PMID[468326]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	439.9	n.a.	PMID[468326]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	434.2	n.a.	PMID[468326]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	254.3	n.a.	PMID[468326]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	256.5	n.a.	PMID[468326]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	10.3	n.a.	PMID[468326]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	25.9	n.a.	PMID[468326]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	1.0	n.a.	PMID[468326]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	1.9	n.a.	PMID[468326]

☑ 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 NPC31985 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	168
0.1-0.2	1057
0.2-0.3	4569
0.3-0.4	12479
0.4-0.5	9813
0.5-0.6	5993
0.6-0.7	5071
0.7-0.8	2973
0.8-0.85	413
0.85-0.9	106
0.9-0.95	46
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC1015
0.9759	High Similarity	NPC475740
0.9639	High Similarity	NPC474733
0.9639	High Similarity	NPC145879
0.9639	High Similarity	NPC31564
0.9639	High Similarity	NPC474732
0.9639	High Similarity	NPC474778
0.9524	High Similarity	NPC58063
0.9419	High Similarity	NPC48010
0.9412	High Similarity	NPC471722
0.9398	High Similarity	NPC214043
0.9398	High Similarity	NPC221758
0.9398	High Similarity	NPC59453
0.9398	High Similarity	NPC85774
0.9318	High Similarity	NPC196485
0.9318	High Similarity	NPC245972
0.9302	High Similarity	NPC26959
0.9302	High Similarity	NPC268406
0.9302	High Similarity	NPC32830
0.9302	High Similarity	NPC474245
0.9302	High Similarity	NPC186688
0.9286	High Similarity	NPC470574
0.9286	High Similarity	NPC469948
0.9205	High Similarity	NPC475255
0.9186	High Similarity	NPC328539
0.9176	High Similarity	NPC475022
0.9176	High Similarity	NPC72133
0.9176	High Similarity	NPC118648
0.9176	High Similarity	NPC222613
0.9176	High Similarity	NPC51014
0.9167	High Similarity	NPC472265
0.9167	High Similarity	NPC473246
0.9157	High Similarity	NPC151519
0.9101	High Similarity	NPC111015
0.9091	High Similarity	NPC272746
0.9091	High Similarity	NPC473998
0.9091	High Similarity	NPC185936
0.9091	High Similarity	NPC155304
0.9091	High Similarity	NPC168027
0.9091	High Similarity	NPC131872
0.908	High Similarity	NPC475921
0.908	High Similarity	NPC473999
0.908	High Similarity	NPC119416
0.908	High Similarity	NPC309603
0.908	High Similarity	NPC474704
0.908	High Similarity	NPC477943
0.908	High Similarity	NPC86319
0.908	High Similarity	NPC275740
0.907	High Similarity	NPC90652
0.9059	High Similarity	NPC197823
0.9011	High Similarity	NPC108078
0.9	High Similarity	NPC473170
0.8989	High Similarity	NPC472930
0.8989	High Similarity	NPC12722
0.8977	High Similarity	NPC126993
0.8977	High Similarity	NPC191684
0.8977	High Similarity	NPC85173
0.8966	High Similarity	NPC292491
0.8966	High Similarity	NPC53911
0.8966	High Similarity	NPC143767
0.8966	High Similarity	NPC328313
0.8966	High Similarity	NPC131470
0.8966	High Similarity	NPC470417
0.8966	High Similarity	NPC310752
0.8953	High Similarity	NPC155011
0.8941	High Similarity	NPC321187
0.8941	High Similarity	NPC329043
0.8941	High Similarity	NPC82902
0.8941	High Similarity	NPC237712
0.8941	High Similarity	NPC33913
0.8941	High Similarity	NPC161423
0.8941	High Similarity	NPC58841
0.8941	High Similarity	NPC227064
0.8916	High Similarity	NPC2482
0.8889	High Similarity	NPC474690
0.8889	High Similarity	NPC8993
0.8889	High Similarity	NPC166906
0.8876	High Similarity	NPC475806
0.8864	High Similarity	NPC76879
0.8864	High Similarity	NPC250592
0.8864	High Similarity	NPC310010
0.8864	High Similarity	NPC326627
0.8864	High Similarity	NPC77263
0.8851	High Similarity	NPC474684
0.8851	High Similarity	NPC142361
0.8851	High Similarity	NPC93778
0.8851	High Similarity	NPC141292
0.8851	High Similarity	NPC317590
0.8837	High Similarity	NPC471224
0.8837	High Similarity	NPC474218
0.8824	High Similarity	NPC278648
0.8824	High Similarity	NPC476082
0.8804	High Similarity	NPC18509
0.8791	High Similarity	NPC470016
0.8791	High Similarity	NPC472932
0.8791	High Similarity	NPC317586
0.8791	High Similarity	NPC271195
0.8778	High Similarity	NPC474736
0.8778	High Similarity	NPC69454
0.8764	High Similarity	NPC171441
0.8764	High Similarity	NPC183283
0.875	High Similarity	NPC193360
0.875	High Similarity	NPC242864
0.875	High Similarity	NPC471724
0.875	High Similarity	NPC474677
0.8737	High Similarity	NPC249187
0.8737	High Similarity	NPC247957
0.8736	High Similarity	NPC94755
0.8736	High Similarity	NPC94666
0.8736	High Similarity	NPC469994
0.8736	High Similarity	NPC20688
0.8736	High Similarity	NPC327115
0.871	High Similarity	NPC114274
0.8696	High Similarity	NPC249954
0.8696	High Similarity	NPC305483
0.8696	High Similarity	NPC192428
0.8696	High Similarity	NPC328162
0.8696	High Similarity	NPC96859
0.869	High Similarity	NPC472478
0.8681	High Similarity	NPC292793
0.8667	High Similarity	NPC189520
0.8667	High Similarity	NPC86266
0.8667	High Similarity	NPC233116
0.8667	High Similarity	NPC212301
0.8667	High Similarity	NPC63748
0.8667	High Similarity	NPC110657
0.8646	High Similarity	NPC72255
0.8636	High Similarity	NPC96496
0.8636	High Similarity	NPC187376
0.8636	High Similarity	NPC159046
0.8636	High Similarity	NPC233836
0.8636	High Similarity	NPC136548
0.8621	High Similarity	NPC474083
0.8621	High Similarity	NPC202868
0.8617	High Similarity	NPC154072
0.8617	High Similarity	NPC83709
0.8617	High Similarity	NPC144956
0.8602	High Similarity	NPC474938
0.8602	High Similarity	NPC474785
0.8602	High Similarity	NPC320306
0.8602	High Similarity	NPC190554
0.8588	High Similarity	NPC136150
0.8588	High Similarity	NPC121984
0.8587	High Similarity	NPC180950
0.8587	High Similarity	NPC469995
0.8587	High Similarity	NPC318282
0.8587	High Similarity	NPC174948
0.8587	High Similarity	NPC469599
0.8587	High Similarity	NPC259286
0.8587	High Similarity	NPC173875
0.8587	High Similarity	NPC88310
0.8571	High Similarity	NPC474807
0.8571	High Similarity	NPC109305
0.8571	High Similarity	NPC470376
0.8571	High Similarity	NPC233118
0.8571	High Similarity	NPC250575
0.8571	High Similarity	NPC170220
0.8571	High Similarity	NPC134826
0.8571	High Similarity	NPC107674
0.8571	High Similarity	NPC472942
0.8571	High Similarity	NPC141497
0.8571	High Similarity	NPC470375
0.8557	High Similarity	NPC257353
0.8557	High Similarity	NPC60681
0.8556	High Similarity	NPC471896
0.8556	High Similarity	NPC320026
0.8539	High Similarity	NPC472802
0.8539	High Similarity	NPC206060
0.8539	High Similarity	NPC44181
0.8523	High Similarity	NPC28252
0.8523	High Similarity	NPC55309
0.8523	High Similarity	NPC213412
0.8523	High Similarity	NPC473168
0.8523	High Similarity	NPC158393
0.8511	High Similarity	NPC103051
0.8506	High Similarity	NPC180834
0.8506	High Similarity	NPC25833
0.8495	Intermediate Similarity	NPC471153
0.8495	Intermediate Similarity	NPC471463
0.8495	Intermediate Similarity	NPC117133
0.8495	Intermediate Similarity	NPC472941
0.8495	Intermediate Similarity	NPC456
0.8495	Intermediate Similarity	NPC328371
0.8488	Intermediate Similarity	NPC101462
0.8488	Intermediate Similarity	NPC320514
0.8488	Intermediate Similarity	NPC193347
0.8488	Intermediate Similarity	NPC212083
0.8488	Intermediate Similarity	NPC328351
0.8488	Intermediate Similarity	NPC48362
0.8478	Intermediate Similarity	NPC67831
0.8478	Intermediate Similarity	NPC209662
0.8478	Intermediate Similarity	NPC299100
0.8478	Intermediate Similarity	NPC23170
0.8478	Intermediate Similarity	NPC174051
0.8478	Intermediate Similarity	NPC49670
0.8478	Intermediate Similarity	NPC473172
0.8469	Intermediate Similarity	NPC185
0.8462	Intermediate Similarity	NPC145067
0.8462	Intermediate Similarity	NPC233455
0.8462	Intermediate Similarity	NPC297265

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 NPC31985 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1354
0.2-0.3	3950
0.3-0.4	2538
0.4-0.5	655
0.5-0.6	169
0.6-0.7	110
0.7-0.8	137
0.8-0.85	63
0.85-0.9	21
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9398	High Similarity	NPD4786	Approved
0.9302	High Similarity	NPD5328	Approved
0.9176	High Similarity	NPD3618	Phase 1
0.9157	High Similarity	NPD3667	Approved
0.9091	High Similarity	NPD6079	Approved
0.8941	High Similarity	NPD3665	Phase 1
0.8941	High Similarity	NPD3133	Approved
0.8941	High Similarity	NPD3666	Approved
0.8864	High Similarity	NPD4753	Phase 2
0.8804	High Similarity	NPD4755	Approved
0.8778	High Similarity	NPD4202	Approved
0.8696	High Similarity	NPD5222	Approved
0.8696	High Similarity	NPD5220	Clinical (unspecified phase)
0.8696	High Similarity	NPD5221	Approved
0.8696	High Similarity	NPD4697	Phase 3
0.8617	High Similarity	NPD5286	Approved
0.8617	High Similarity	NPD5285	Approved
0.8617	High Similarity	NPD4700	Approved
0.8617	High Similarity	NPD4696	Approved
0.8602	High Similarity	NPD5173	Approved
0.8571	High Similarity	NPD6399	Phase 3
0.8523	High Similarity	NPD5279	Phase 3
0.8506	High Similarity	NPD3668	Phase 3
0.8488	Intermediate Similarity	NPD4221	Approved
0.8488	Intermediate Similarity	NPD4223	Phase 3
0.8462	Intermediate Similarity	NPD7515	Phase 2
0.8438	Intermediate Similarity	NPD5226	Approved
0.8438	Intermediate Similarity	NPD5224	Approved
0.8438	Intermediate Similarity	NPD5225	Approved
0.8438	Intermediate Similarity	NPD5211	Phase 2
0.8438	Intermediate Similarity	NPD4633	Approved
0.8409	Intermediate Similarity	NPD5329	Approved
0.8404	Intermediate Similarity	NPD6084	Phase 2
0.8404	Intermediate Similarity	NPD6083	Phase 2
0.8387	Intermediate Similarity	NPD4629	Approved
0.8387	Intermediate Similarity	NPD5210	Approved
0.8367	Intermediate Similarity	NPD6675	Approved
0.8367	Intermediate Similarity	NPD5739	Approved
0.8367	Intermediate Similarity	NPD7128	Approved
0.8367	Intermediate Similarity	NPD6402	Approved
0.8351	Intermediate Similarity	NPD5175	Approved
0.8351	Intermediate Similarity	NPD5174	Approved
0.8333	Intermediate Similarity	NPD5223	Approved
0.8313	Intermediate Similarity	NPD7339	Approved
0.8313	Intermediate Similarity	NPD6942	Approved
0.8295	Intermediate Similarity	NPD4197	Approved
0.8265	Intermediate Similarity	NPD5141	Approved
0.82	Intermediate Similarity	NPD7320	Approved
0.82	Intermediate Similarity	NPD6899	Approved
0.82	Intermediate Similarity	NPD6881	Approved
0.8182	Intermediate Similarity	NPD4767	Approved
0.8182	Intermediate Similarity	NPD4768	Approved
0.8163	Intermediate Similarity	NPD4754	Approved
0.8132	Intermediate Similarity	NPD6672	Approved
0.8132	Intermediate Similarity	NPD5737	Approved
0.8119	Intermediate Similarity	NPD6372	Approved
0.8119	Intermediate Similarity	NPD6373	Approved
0.8111	Intermediate Similarity	NPD7521	Approved
0.8111	Intermediate Similarity	NPD6409	Approved
0.8111	Intermediate Similarity	NPD7334	Approved
0.8111	Intermediate Similarity	NPD4693	Phase 3
0.8111	Intermediate Similarity	NPD4690	Approved
0.8111	Intermediate Similarity	NPD6684	Approved
0.8111	Intermediate Similarity	NPD4688	Approved
0.8111	Intermediate Similarity	NPD5205	Approved
0.8111	Intermediate Similarity	NPD4689	Approved
0.8111	Intermediate Similarity	NPD7146	Approved
0.8111	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD5330	Approved
0.8111	Intermediate Similarity	NPD4138	Approved
0.81	Intermediate Similarity	NPD5697	Approved
0.81	Intermediate Similarity	NPD5701	Approved
0.8085	Intermediate Similarity	NPD7748	Approved
0.8046	Intermediate Similarity	NPD4695	Discontinued
0.8046	Intermediate Similarity	NPD7525	Registered
0.8039	Intermediate Similarity	NPD7102	Approved
0.8039	Intermediate Similarity	NPD7290	Approved
0.8039	Intermediate Similarity	NPD6883	Approved
0.8023	Intermediate Similarity	NPD3617	Approved
0.802	Intermediate Similarity	NPD5128	Approved
0.802	Intermediate Similarity	NPD4730	Approved
0.802	Intermediate Similarity	NPD4729	Approved
0.8	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5695	Phase 3
0.7978	Intermediate Similarity	NPD4788	Approved
0.7961	Intermediate Similarity	NPD8130	Phase 1
0.7961	Intermediate Similarity	NPD6617	Approved
0.7961	Intermediate Similarity	NPD6869	Approved
0.7961	Intermediate Similarity	NPD6649	Approved
0.7961	Intermediate Similarity	NPD6847	Approved
0.7961	Intermediate Similarity	NPD6650	Approved
0.7941	Intermediate Similarity	NPD6014	Approved
0.7941	Intermediate Similarity	NPD6012	Approved
0.7941	Intermediate Similarity	NPD6013	Approved
0.7938	Intermediate Similarity	NPD5696	Approved
0.7935	Intermediate Similarity	NPD6903	Approved
0.7935	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD5690	Phase 2
0.7912	Intermediate Similarity	NPD5280	Approved
0.7912	Intermediate Similarity	NPD4694	Approved
0.7885	Intermediate Similarity	NPD8297	Approved
0.7885	Intermediate Similarity	NPD6882	Approved
0.7864	Intermediate Similarity	NPD5249	Phase 3
0.7864	Intermediate Similarity	NPD5248	Approved
0.7864	Intermediate Similarity	NPD5247	Approved
0.7864	Intermediate Similarity	NPD4634	Approved
0.7864	Intermediate Similarity	NPD5250	Approved
0.7864	Intermediate Similarity	NPD5251	Approved
0.7843	Intermediate Similarity	NPD6011	Approved
0.7843	Intermediate Similarity	NPD5168	Approved
0.7835	Intermediate Similarity	NPD7902	Approved
0.7831	Intermediate Similarity	NPD4747	Approved
0.7788	Intermediate Similarity	NPD5217	Approved
0.7788	Intermediate Similarity	NPD5216	Approved
0.7788	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD5215	Approved
0.7757	Intermediate Similarity	NPD7115	Discovery
0.7755	Intermediate Similarity	NPD7638	Approved
0.7745	Intermediate Similarity	NPD6412	Phase 2
0.7727	Intermediate Similarity	NPD4195	Approved
0.7711	Intermediate Similarity	NPD4137	Phase 3
0.7692	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5135	Approved
0.7692	Intermediate Similarity	NPD5169	Approved
0.7684	Intermediate Similarity	NPD5284	Approved
0.7684	Intermediate Similarity	NPD5281	Approved
0.7677	Intermediate Similarity	NPD7640	Approved
0.7677	Intermediate Similarity	NPD7639	Approved
0.766	Intermediate Similarity	NPD6080	Approved
0.766	Intermediate Similarity	NPD6904	Approved
0.766	Intermediate Similarity	NPD6673	Approved
0.7629	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4691	Approved
0.7619	Intermediate Similarity	NPD5127	Approved
0.7558	Intermediate Similarity	NPD6924	Approved
0.7558	Intermediate Similarity	NPD6926	Approved
0.7558	Intermediate Similarity	NPD5733	Approved
0.7529	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7645	Phase 2
0.7527	Intermediate Similarity	NPD4623	Approved
0.7527	Intermediate Similarity	NPD4519	Discontinued
0.7526	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7900	Approved
0.75	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD8034	Phase 2
0.75	Intermediate Similarity	NPD6868	Approved
0.75	Intermediate Similarity	NPD6274	Approved
0.7477	Intermediate Similarity	NPD4632	Approved
0.7476	Intermediate Similarity	NPD6008	Approved
0.7474	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7101	Approved
0.7455	Intermediate Similarity	NPD7100	Approved
0.7407	Intermediate Similarity	NPD5167	Approved
0.7396	Intermediate Similarity	NPD4096	Approved
0.7387	Intermediate Similarity	NPD6054	Approved
0.7387	Intermediate Similarity	NPD6059	Approved
0.7386	Intermediate Similarity	NPD6933	Approved
0.7386	Intermediate Similarity	NPD6117	Approved
0.7368	Intermediate Similarity	NPD5208	Approved
0.7368	Intermediate Similarity	NPD4518	Approved
0.7364	Intermediate Similarity	NPD6335	Approved
0.7363	Intermediate Similarity	NPD4139	Approved
0.7363	Intermediate Similarity	NPD4692	Approved
0.7356	Intermediate Similarity	NPD4687	Approved
0.7356	Intermediate Similarity	NPD4784	Approved
0.7356	Intermediate Similarity	NPD4785	Approved
0.7356	Intermediate Similarity	NPD4058	Approved
0.734	Intermediate Similarity	NPD6098	Approved
0.7333	Intermediate Similarity	NPD6929	Approved
0.7326	Intermediate Similarity	NPD7151	Approved
0.7326	Intermediate Similarity	NPD5276	Approved
0.7326	Intermediate Similarity	NPD7152	Approved
0.7326	Intermediate Similarity	NPD7150	Approved
0.7326	Intermediate Similarity	NPD4243	Approved
0.7321	Intermediate Similarity	NPD6909	Approved
0.7321	Intermediate Similarity	NPD6908	Approved
0.732	Intermediate Similarity	NPD5693	Phase 1
0.732	Intermediate Similarity	NPD6050	Approved
0.7303	Intermediate Similarity	NPD6116	Phase 1
0.7294	Intermediate Similarity	NPD6922	Approved
0.7294	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6923	Approved
0.7294	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6317	Approved
0.7273	Intermediate Similarity	NPD6009	Approved
0.7263	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6370	Approved
0.7253	Intermediate Similarity	NPD6931	Approved
0.7253	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6930	Phase 2
0.7245	Intermediate Similarity	NPD5133	Approved
0.7232	Intermediate Similarity	NPD6319	Approved
0.7229	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5290	Discontinued
0.7222	Intermediate Similarity	NPD6118	Approved
0.7222	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6115	Approved
0.7222	Intermediate Similarity	NPD6114	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