NPASS Compound

Structure

NPC2783 OpenBabel07101718242D 34 38 0 0 1 0 0 0 0 0999 V2000 -4.7123 -0.9432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1072 -1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5058 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0186 -0.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0308 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4581 1.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7592 -0.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4581 0.1861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5315 -2.4359 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1352 2.3517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 -2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1661 2.4535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7079 3.1399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 13 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 27 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 18 17 1 6 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 19 28 1 6 0 0 0 20 24 1 0 0 0 0 20 31 1 6 0 0 0 21 26 1 0 0 0 0 21 27 1 1 0 0 0 22 26 1 0 0 0 0 22 32 1 6 0 0 0 23 30 1 1 0 0 0 24 27 1 1 0 0 0 24 29 1 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	5.035
LogD:	4.587
LogS:	-4.226
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	4.922
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.375
MDCK Permeability:	7.777030987199396e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.912

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	85.0934829711914%
Volume Distribution (VD):	0.573
Pgp-substrate:	6.82757043838501%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.429
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.21
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.27
CYP3A4-inhibitor:	0.291
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	2.074
Half-life (T1/2):	0.264

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.29
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.756
Skin Sensitization:	0.169
Carcinogencity:	0.005
Eye Corrosion:	0.119
Eye Irritation:	0.278
Respiratory Toxicity:	0.903

Download Data

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

Natural Product: NPC2783

Natural Product ID:	NPC2783
*Common Name:**	Impressic Acid
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,9R,11aS,11bR,12R,13aR,13bR)-9,12-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms:	Impressic Acid
Standard InCHIKey:	CQYNGKPLHGNVHC-LEBDGTJJSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-17(2)18-8-13-30(25(33)34)15-14-28(6)19(23(18)30)16-20(31)24-27(5)11-10-22(32)26(3,4)21(27)9-12-29(24,28)7/h18-24,31-32H,1,8-16H2,2-7H3,(H,33,34)/t18-,19+,20+,21-,22+,23+,24+,27-,28+,29+,30-/m0/s1
SMILES:	O[C@@H]1C[C@@H]2[C@H]3[C@@H](CC[C@@]3(CC[C@]2([C@]2([C@H]1[C@@]1(C)CC[C@H](C([C@@H]1CC2)(C)C)O)C)C)C(=O)O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1271693
PubChem CID:	15038462
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29834	Acanthopanax koreanum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20621475]
NPO29834	Acanthopanax koreanum	n.a.	n.a.	n.a.	steamed leaves	n.a.	n.a.	PMID[20932756]
NPO29834	Acanthopanax koreanum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Others	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	62.6	%	PMID[530510]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	67.9	%	PMID[530510]

☑ 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 NPC2783 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	191
0.1-0.2	1615
0.2-0.3	6734
0.3-0.4	15792
0.4-0.5	6106
0.5-0.6	4762
0.6-0.7	4560
0.7-0.8	2391
0.8-0.85	370
0.85-0.9	125
0.9-0.95	30
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC269360
0.9877	High Similarity	NPC264005
0.9877	High Similarity	NPC33768
0.9875	High Similarity	NPC264317
0.9875	High Similarity	NPC294438
0.9756	High Similarity	NPC474719
0.9756	High Similarity	NPC16377
0.9753	High Similarity	NPC12774
0.9639	High Similarity	NPC213832
0.9639	High Similarity	NPC57954
0.9639	High Similarity	NPC220498
0.9524	High Similarity	NPC169933
0.9518	High Similarity	NPC4309
0.9518	High Similarity	NPC471900
0.9405	High Similarity	NPC271974
0.9405	High Similarity	NPC247312
0.9383	High Similarity	NPC475726
0.9383	High Similarity	NPC472743
0.9302	High Similarity	NPC291373
0.9302	High Similarity	NPC287118
0.9302	High Similarity	NPC244356
0.9302	High Similarity	NPC473690
0.9302	High Similarity	NPC224060
0.9302	High Similarity	NPC471902
0.9268	High Similarity	NPC264665
0.9268	High Similarity	NPC474482
0.9268	High Similarity	NPC475745
0.9268	High Similarity	NPC74595
0.9195	High Similarity	NPC277399
0.9186	High Similarity	NPC475416
0.9186	High Similarity	NPC160506
0.9186	High Similarity	NPC471901
0.9157	High Similarity	NPC98270
0.9157	High Similarity	NPC292553
0.9157	High Similarity	NPC201655
0.9146	High Similarity	NPC471037
0.9059	High Similarity	NPC146937
0.9048	High Similarity	NPC269396
0.9048	High Similarity	NPC472738
0.9048	High Similarity	NPC187545
0.9048	High Similarity	NPC98236
0.9036	High Similarity	NPC475509
0.9036	High Similarity	NPC474233
0.8977	High Similarity	NPC303863
0.8953	High Similarity	NPC475921
0.8953	High Similarity	NPC474704
0.8941	High Similarity	NPC57469
0.8941	High Similarity	NPC474684
0.8941	High Similarity	NPC142361
0.8941	High Similarity	NPC4643
0.8916	High Similarity	NPC245866
0.8916	High Similarity	NPC5280
0.8889	High Similarity	NPC192744
0.8889	High Similarity	NPC201459
0.8875	High Similarity	NPC298168
0.8875	High Similarity	NPC68828
0.8875	High Similarity	NPC143133
0.8864	High Similarity	NPC475061
0.8837	High Similarity	NPC242864
0.8837	High Similarity	NPC472739
0.8837	High Similarity	NPC52169
0.8837	High Similarity	NPC182797
0.8824	High Similarity	NPC55309
0.8824	High Similarity	NPC70661
0.8824	High Similarity	NPC28252
0.8824	High Similarity	NPC168231
0.8824	High Similarity	NPC80590
0.875	High Similarity	NPC4209
0.875	High Similarity	NPC189520
0.875	High Similarity	NPC246445
0.8736	High Similarity	NPC234346
0.8736	High Similarity	NPC293048
0.8736	High Similarity	NPC225585
0.8736	High Similarity	NPC270768
0.8736	High Similarity	NPC127689
0.8736	High Similarity	NPC25906
0.8736	High Similarity	NPC198664
0.8736	High Similarity	NPC130520
0.8736	High Similarity	NPC274330
0.8736	High Similarity	NPC59263
0.8736	High Similarity	NPC143232
0.8736	High Similarity	NPC121798
0.8736	High Similarity	NPC263393
0.8736	High Similarity	NPC64872
0.8736	High Similarity	NPC61543
0.8736	High Similarity	NPC290972
0.8721	High Similarity	NPC142415
0.8721	High Similarity	NPC159046
0.8721	High Similarity	NPC242468
0.8721	High Similarity	NPC307426
0.8721	High Similarity	NPC233836
0.8721	High Similarity	NPC102683
0.8721	High Similarity	NPC293564
0.8721	High Similarity	NPC88716
0.8721	High Similarity	NPC68160
0.8721	High Similarity	NPC187376
0.8721	High Similarity	NPC171203
0.8721	High Similarity	NPC18064
0.8721	High Similarity	NPC51700
0.8721	High Similarity	NPC130577
0.8721	High Similarity	NPC98442
0.8721	High Similarity	NPC134197
0.8706	High Similarity	NPC76518
0.8675	High Similarity	NPC474484
0.8675	High Similarity	NPC103754
0.8667	High Similarity	NPC288906
0.8667	High Similarity	NPC205173
0.8667	High Similarity	NPC279974
0.8667	High Similarity	NPC263135
0.8667	High Similarity	NPC266431
0.8652	High Similarity	NPC470376
0.8652	High Similarity	NPC294263
0.8652	High Similarity	NPC470375
0.8642	High Similarity	NPC66105
0.8642	High Similarity	NPC207010
0.8642	High Similarity	NPC317913
0.8642	High Similarity	NPC474433
0.8636	High Similarity	NPC120968
0.8636	High Similarity	NPC477872
0.8636	High Similarity	NPC7260
0.8636	High Similarity	NPC18872
0.8636	High Similarity	NPC227467
0.8636	High Similarity	NPC470589
0.8636	High Similarity	NPC469400
0.8636	High Similarity	NPC126369
0.8636	High Similarity	NPC130278
0.8636	High Similarity	NPC471896
0.8636	High Similarity	NPC111110
0.8636	High Similarity	NPC210037
0.8636	High Similarity	NPC290614
0.8636	High Similarity	NPC291028
0.8636	High Similarity	NPC273621
0.8625	High Similarity	NPC240235
0.8625	High Similarity	NPC212733
0.8625	High Similarity	NPC104387
0.8625	High Similarity	NPC178383
0.8625	High Similarity	NPC212879
0.8625	High Similarity	NPC231256
0.8621	High Similarity	NPC470629
0.8621	High Similarity	NPC211162
0.8621	High Similarity	NPC290690
0.8621	High Similarity	NPC246708
0.8621	High Similarity	NPC40552
0.8621	High Similarity	NPC183374
0.8621	High Similarity	NPC17733
0.8621	High Similarity	NPC474512
0.8621	High Similarity	NPC181225
0.8621	High Similarity	NPC473242
0.8605	High Similarity	NPC72638
0.8605	High Similarity	NPC155011
0.8588	High Similarity	NPC263974
0.8571	High Similarity	NPC289486
0.8571	High Similarity	NPC61107
0.8571	High Similarity	NPC30583
0.8571	High Similarity	NPC170985
0.8571	High Similarity	NPC234564
0.8556	High Similarity	NPC47853
0.8554	High Similarity	NPC304194
0.8554	High Similarity	NPC261616
0.8554	High Similarity	NPC164999
0.8554	High Similarity	NPC206735
0.8539	High Similarity	NPC84319
0.8539	High Similarity	NPC235884
0.8539	High Similarity	NPC145067
0.8539	High Similarity	NPC472149
0.8539	High Similarity	NPC25299
0.8539	High Similarity	NPC155120
0.8539	High Similarity	NPC198242
0.8539	High Similarity	NPC23434
0.8539	High Similarity	NPC306541
0.8539	High Similarity	NPC211403
0.8539	High Similarity	NPC4036
0.8539	High Similarity	NPC187722
0.8539	High Similarity	NPC233455
0.8539	High Similarity	NPC228784
0.8539	High Similarity	NPC105189
0.8539	High Similarity	NPC86266
0.8539	High Similarity	NPC474525
0.8539	High Similarity	NPC288833
0.8539	High Similarity	NPC324341
0.8539	High Similarity	NPC158030
0.8539	High Similarity	NPC52021
0.8539	High Similarity	NPC282616
0.8539	High Similarity	NPC110657
0.8539	High Similarity	NPC966
0.8539	High Similarity	NPC212301
0.8539	High Similarity	NPC71074
0.8539	High Similarity	NPC300351
0.8539	High Similarity	NPC65120
0.8537	High Similarity	NPC63020
0.8537	High Similarity	NPC34046
0.8537	High Similarity	NPC324700
0.8537	High Similarity	NPC224802
0.8537	High Similarity	NPC80089
0.8537	High Similarity	NPC171426
0.8523	High Similarity	NPC95246
0.8523	High Similarity	NPC84271
0.8523	High Similarity	NPC474889
0.8523	High Similarity	NPC77168
0.8523	High Similarity	NPC102414

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 NPC2783 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	2027
0.2-0.3	4145
0.3-0.4	1895
0.4-0.5	470
0.5-0.6	149
0.6-0.7	178
0.7-0.8	105
0.8-0.85	7
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9875	High Similarity	NPD7520	Clinical (unspecified phase)
0.9186	High Similarity	NPD8034	Phase 2
0.9186	High Similarity	NPD8035	Phase 2
0.875	High Similarity	NPD6117	Approved
0.8642	High Similarity	NPD6116	Phase 1
0.8539	High Similarity	NPD7515	Phase 2
0.8537	High Similarity	NPD6697	Approved
0.8537	High Similarity	NPD6114	Approved
0.8537	High Similarity	NPD6118	Approved
0.8537	High Similarity	NPD6115	Approved
0.85	High Similarity	NPD6113	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD4786	Approved
0.8152	Intermediate Similarity	NPD7748	Approved
0.8111	Intermediate Similarity	NPD5328	Approved
0.8046	Intermediate Similarity	NPD4788	Approved
0.8043	Intermediate Similarity	NPD6399	Phase 3
0.8025	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD3618	Phase 1
0.7935	Intermediate Similarity	NPD6079	Approved
0.7931	Intermediate Similarity	NPD3667	Approved
0.7907	Intermediate Similarity	NPD7525	Registered
0.7895	Intermediate Similarity	NPD7902	Approved
0.7812	Intermediate Similarity	NPD7638	Approved
0.7778	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD7639	Approved
0.7732	Intermediate Similarity	NPD7640	Approved
0.77	Intermediate Similarity	NPD7128	Approved
0.77	Intermediate Similarity	NPD5739	Approved
0.77	Intermediate Similarity	NPD6675	Approved
0.77	Intermediate Similarity	NPD6402	Approved
0.766	Intermediate Similarity	NPD4202	Approved
0.7609	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD4697	Phase 3
0.7604	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD5222	Approved
0.7604	Intermediate Similarity	NPD5221	Approved
0.759	Intermediate Similarity	NPD6081	Approved
0.7579	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7900	Approved
0.7556	Intermediate Similarity	NPD3665	Phase 1
0.7556	Intermediate Similarity	NPD3666	Approved
0.7556	Intermediate Similarity	NPD3133	Approved
0.7549	Intermediate Similarity	NPD6899	Approved
0.7549	Intermediate Similarity	NPD6881	Approved
0.7549	Intermediate Similarity	NPD7320	Approved
0.7529	Intermediate Similarity	NPD3703	Phase 2
0.7526	Intermediate Similarity	NPD6084	Phase 2
0.7526	Intermediate Similarity	NPD6083	Phase 2
0.7526	Intermediate Similarity	NPD4755	Approved
0.7526	Intermediate Similarity	NPD5173	Approved
0.7476	Intermediate Similarity	NPD6373	Approved
0.7476	Intermediate Similarity	NPD6372	Approved
0.747	Intermediate Similarity	NPD4244	Approved
0.747	Intermediate Similarity	NPD4789	Approved
0.747	Intermediate Similarity	NPD4245	Approved
0.7451	Intermediate Similarity	NPD5697	Approved
0.7451	Intermediate Similarity	NPD5701	Approved
0.7439	Intermediate Similarity	NPD5360	Phase 3
0.7439	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6672	Approved
0.7419	Intermediate Similarity	NPD5737	Approved
0.7407	Intermediate Similarity	NPD4224	Phase 2
0.7404	Intermediate Similarity	NPD7290	Approved
0.7404	Intermediate Similarity	NPD6883	Approved
0.7404	Intermediate Similarity	NPD7102	Approved
0.7391	Intermediate Similarity	NPD6684	Approved
0.7391	Intermediate Similarity	NPD5330	Approved
0.7391	Intermediate Similarity	NPD7146	Approved
0.7391	Intermediate Similarity	NPD6409	Approved
0.7391	Intermediate Similarity	NPD7334	Approved
0.7391	Intermediate Similarity	NPD7521	Approved
0.7386	Intermediate Similarity	NPD7645	Phase 2
0.7379	Intermediate Similarity	NPD6011	Approved
0.7374	Intermediate Similarity	NPD5286	Approved
0.7374	Intermediate Similarity	NPD4700	Approved
0.7374	Intermediate Similarity	NPD4696	Approved
0.7374	Intermediate Similarity	NPD5285	Approved
0.7363	Intermediate Similarity	NPD3668	Phase 3
0.7349	Intermediate Similarity	NPD3698	Phase 2
0.734	Intermediate Similarity	NPD4753	Phase 2
0.7333	Intermediate Similarity	NPD6869	Approved
0.7333	Intermediate Similarity	NPD8130	Phase 1
0.7333	Intermediate Similarity	NPD6617	Approved
0.7333	Intermediate Similarity	NPD6649	Approved
0.7333	Intermediate Similarity	NPD6847	Approved
0.7333	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6650	Approved
0.7326	Intermediate Similarity	NPD6942	Approved
0.7326	Intermediate Similarity	NPD7339	Approved
0.7308	Intermediate Similarity	NPD6012	Approved
0.7308	Intermediate Similarity	NPD6014	Approved
0.7308	Intermediate Similarity	NPD6013	Approved
0.73	Intermediate Similarity	NPD5223	Approved
0.7284	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6882	Approved
0.7264	Intermediate Similarity	NPD8297	Approved
0.7234	Intermediate Similarity	NPD6903	Approved
0.7228	Intermediate Similarity	NPD5224	Approved
0.7228	Intermediate Similarity	NPD7632	Discontinued
0.7228	Intermediate Similarity	NPD5226	Approved
0.7228	Intermediate Similarity	NPD4633	Approved
0.7228	Intermediate Similarity	NPD5225	Approved
0.7228	Intermediate Similarity	NPD5211	Phase 2
0.7204	Intermediate Similarity	NPD5279	Phase 3
0.7196	Intermediate Similarity	NPD8133	Approved
0.7176	Intermediate Similarity	NPD5777	Approved
0.7157	Intermediate Similarity	NPD5175	Approved
0.7157	Intermediate Similarity	NPD5174	Approved
0.7157	Intermediate Similarity	NPD4754	Approved
0.7156	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3702	Approved
0.71	Intermediate Similarity	NPD5696	Approved
0.7097	Intermediate Similarity	NPD5329	Approved
0.7087	Intermediate Similarity	NPD5141	Approved
0.7079	Intermediate Similarity	NPD3671	Phase 1
0.7079	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6868	Approved
0.7045	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4632	Approved
0.7021	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6098	Approved
0.7019	Intermediate Similarity	NPD4767	Approved
0.7019	Intermediate Similarity	NPD4768	Approved
0.701	Intermediate Similarity	NPD5284	Approved
0.701	Intermediate Similarity	NPD5281	Approved
0.6989	Remote Similarity	NPD4197	Approved
0.6979	Remote Similarity	NPD6673	Approved
0.6979	Remote Similarity	NPD6904	Approved
0.6979	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6080	Approved
0.6977	Remote Similarity	NPD4758	Discontinued
0.697	Remote Similarity	NPD4629	Approved
0.697	Remote Similarity	NPD5210	Approved
0.6937	Remote Similarity	NPD6335	Approved
0.6909	Remote Similarity	NPD6274	Approved
0.6889	Remote Similarity	NPD5364	Discontinued
0.6889	Remote Similarity	NPD3617	Approved
0.6887	Remote Similarity	NPD4729	Approved
0.6887	Remote Similarity	NPD5168	Approved
0.6887	Remote Similarity	NPD5128	Approved
0.6887	Remote Similarity	NPD4730	Approved
0.6875	Remote Similarity	NPD7100	Approved
0.6875	Remote Similarity	NPD7101	Approved
0.6863	Remote Similarity	NPD8418	Phase 2
0.6857	Remote Similarity	NPD6008	Approved
0.6847	Remote Similarity	NPD6317	Approved
0.6847	Remote Similarity	NPD6009	Approved
0.6842	Remote Similarity	NPD5205	Approved
0.6842	Remote Similarity	NPD4138	Approved
0.6842	Remote Similarity	NPD4689	Approved
0.6842	Remote Similarity	NPD4688	Approved
0.6842	Remote Similarity	NPD4690	Approved
0.6842	Remote Similarity	NPD4693	Phase 3
0.6837	Remote Similarity	NPD6411	Approved
0.6818	Remote Similarity	NPD6926	Approved
0.6818	Remote Similarity	NPD6924	Approved
0.681	Remote Similarity	NPD7507	Approved
0.6792	Remote Similarity	NPD6412	Phase 2
0.6786	Remote Similarity	NPD6314	Approved
0.6786	Remote Similarity	NPD6313	Approved
0.6771	Remote Similarity	NPD3573	Approved
0.6759	Remote Similarity	NPD5249	Phase 3
0.6759	Remote Similarity	NPD4634	Approved
0.6759	Remote Similarity	NPD5247	Approved
0.6759	Remote Similarity	NPD5169	Approved
0.6759	Remote Similarity	NPD5135	Approved
0.6759	Remote Similarity	NPD5250	Approved
0.6759	Remote Similarity	NPD5251	Approved
0.6759	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5248	Approved
0.6754	Remote Similarity	NPD6909	Approved
0.6754	Remote Similarity	NPD6908	Approved
0.6702	Remote Similarity	NPD5362	Discontinued
0.6701	Remote Similarity	NPD5208	Approved
0.67	Remote Similarity	NPD6001	Approved
0.6697	Remote Similarity	NPD5217	Approved
0.6697	Remote Similarity	NPD5215	Approved
0.6697	Remote Similarity	NPD5216	Approved
0.6697	Remote Similarity	NPD5127	Approved
0.6695	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7319	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