NPASS Compound

Structure

NPC471897 OpenBabel07101718192D 32 35 0 0 1 0 0 0 0 0999 V2000 -3.3679 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 -2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0518 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3281 -2.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -3.1423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3559 -2.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 0.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3679 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6839 -0.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6839 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3559 -3.9842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5259 1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8420 -1.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8420 0.4861 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 -0.8420 -4.8262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6164 -3.9842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 23 2 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 22 1 0 0 0 0 20 3 1 1 0 0 0 20 21 1 0 0 0 0 21 4 1 6 0 0 0 21 26 1 0 0 0 0 22 28 1 6 0 0 0 23 26 1 0 0 0 0 23 29 1 0 0 0 0 24 28 1 6 0 0 0 24 30 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 26 27 1 1 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.38
Volume:	505.518
LogP:	7.809
LogD:	6.109
LogS:	-6.679
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	4.754
Fsp3:	0.9
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:	-5.174
MDCK Permeability:	9.351801963930484e-06
Pgp-inhibitor:	0.12
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.89
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	97.7365493774414%
Volume Distribution (VD):	0.877
Pgp-substrate:	1.9225974082946777%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.351
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.181
CYP2C9-substrate:	0.794
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.394
CYP3A4-substrate:	0.537

ADMET: Excretion

Clearance (CL):	4.659
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.44
Carcinogencity:	0.082
Eye Corrosion:	0.116
Eye Irritation:	0.086
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC471897

Natural Product ID:	NPC471897
*Common Name:**	4,(23)-Dihydro-Roburic Acid
IUPAC Name:	3-[(1S,2S,4aR,4bS,6aR,9R,10S,10aR,12aR)-1,4a,4b,6a,9,10-hexamethyl-2-propan-2-yl-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid
Synonyms:
Standard InCHIKey:	LJWWZZAOSDWGAX-CSHKLQQTSA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-19(2)22-12-16-30(8)24(28(22,6)15-13-25(31)32)10-9-23-26-21(4)20(3)11-14-27(26,5)17-18-29(23,30)7/h9,19-22,24,26H,10-18H2,1-8H3,(H,31,32)/t20-,21+,22+,24-,26+,27-,28+,29-,30-/m1/s1
SMILES:	CC1CCC2(CCC3(C(=CCC4C3(CCC(C4(C)CCC(=O)O)C(C)C)C)C2C1C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3289102
PubChem CID:	90644336
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
NPO33055	boswellia spp.	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24844534]

☑ 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	3
Others	1

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	10000.0	nM	PMID[543555]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	10000.0	nM	PMID[543555]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	Activity	=	92.4	%	PMID[543555]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	>	10000.0	nM	PMID[543555]

☑ 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 NPC471897 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	178
0.1-0.2	1292
0.2-0.3	6320
0.3-0.4	16288
0.4-0.5	7471
0.5-0.6	5686
0.6-0.7	4015
0.7-0.8	1083
0.8-0.85	278
0.85-0.9	46
0.9-0.95	29
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471899
1.0	High Similarity	NPC107039
0.9861	High Similarity	NPC260385
0.9861	High Similarity	NPC110094
0.9861	High Similarity	NPC280654
0.9859	High Similarity	NPC89294
0.9726	High Similarity	NPC231431
0.9726	High Similarity	NPC16394
0.9726	High Similarity	NPC199595
0.9595	High Similarity	NPC37038
0.9595	High Similarity	NPC104545
0.9467	High Similarity	NPC142244
0.9467	High Similarity	NPC267691
0.9467	High Similarity	NPC263272
0.9467	High Similarity	NPC471898
0.9467	High Similarity	NPC162632
0.9467	High Similarity	NPC221647
0.9467	High Similarity	NPC274050
0.9444	High Similarity	NPC192540
0.9444	High Similarity	NPC279666
0.9342	High Similarity	NPC251779
0.9342	High Similarity	NPC69101
0.9333	High Similarity	NPC477057
0.9315	High Similarity	NPC69143
0.9306	High Similarity	NPC241854
0.9306	High Similarity	NPC283908
0.9306	High Similarity	NPC103958
0.9306	High Similarity	NPC161923
0.9306	High Similarity	NPC183503
0.9306	High Similarity	NPC251970
0.9306	High Similarity	NPC476046
0.9296	High Similarity	NPC160817
0.9221	High Similarity	NPC200752
0.9221	High Similarity	NPC70834
0.9167	High Similarity	NPC36310
0.9103	High Similarity	NPC96095
0.9103	High Similarity	NPC477289
0.9103	High Similarity	NPC156981
0.9054	High Similarity	NPC309399
0.9041	High Similarity	NPC255168
0.8987	High Similarity	NPC474537
0.8961	High Similarity	NPC147066
0.8961	High Similarity	NPC278459
0.8933	High Similarity	NPC165711
0.8919	High Similarity	NPC201027
0.8919	High Similarity	NPC476844
0.8875	High Similarity	NPC324063
0.8831	High Similarity	NPC267517
0.8816	High Similarity	NPC179028
0.8816	High Similarity	NPC321514
0.8784	High Similarity	NPC237591
0.8784	High Similarity	NPC3753
0.8784	High Similarity	NPC166797
0.8784	High Similarity	NPC301065
0.8765	High Similarity	NPC142415
0.8765	High Similarity	NPC158141
0.8765	High Similarity	NPC102683
0.8765	High Similarity	NPC307426
0.8765	High Similarity	NPC242468
0.8765	High Similarity	NPC293564
0.8765	High Similarity	NPC68160
0.8765	High Similarity	NPC88716
0.8765	High Similarity	NPC171203
0.8765	High Similarity	NPC18064
0.8765	High Similarity	NPC98442
0.8765	High Similarity	NPC51700
0.8765	High Similarity	NPC71507
0.8765	High Similarity	NPC130577
0.8765	High Similarity	NPC173089
0.8734	High Similarity	NPC167103
0.8718	High Similarity	NPC201912
0.8718	High Similarity	NPC3915
0.8718	High Similarity	NPC38350
0.8701	High Similarity	NPC327674
0.8701	High Similarity	NPC477371
0.8701	High Similarity	NPC158846
0.8684	High Similarity	NPC68828
0.8667	High Similarity	NPC476795
0.8659	High Similarity	NPC181225
0.8659	High Similarity	NPC17733
0.8659	High Similarity	NPC474512
0.8659	High Similarity	NPC52169
0.8659	High Similarity	NPC473242
0.8659	High Similarity	NPC474474
0.8659	High Similarity	NPC470629
0.8659	High Similarity	NPC290690
0.8659	High Similarity	NPC474511
0.8659	High Similarity	NPC182797
0.8659	High Similarity	NPC40552
0.8659	High Similarity	NPC1753
0.8659	High Similarity	NPC246708
0.8649	High Similarity	NPC244708
0.8649	High Similarity	NPC330659
0.8649	High Similarity	NPC161187
0.8642	High Similarity	NPC72638
0.8611	High Similarity	NPC290445
0.8611	High Similarity	NPC36616
0.8608	High Similarity	NPC310989
0.8608	High Similarity	NPC260956
0.8608	High Similarity	NPC320514
0.8571	High Similarity	NPC239098
0.8554	High Similarity	NPC143232
0.8554	High Similarity	NPC121798
0.8554	High Similarity	NPC263393
0.8554	High Similarity	NPC477973
0.8554	High Similarity	NPC293048
0.8554	High Similarity	NPC25906
0.8554	High Similarity	NPC474972
0.8554	High Similarity	NPC474700
0.8554	High Similarity	NPC274330
0.8554	High Similarity	NPC470588
0.8554	High Similarity	NPC130520
0.8554	High Similarity	NPC161751
0.8554	High Similarity	NPC281524
0.8554	High Similarity	NPC64872
0.8554	High Similarity	NPC290972
0.8554	High Similarity	NPC234346
0.8554	High Similarity	NPC127689
0.8554	High Similarity	NPC198664
0.8554	High Similarity	NPC95246
0.8554	High Similarity	NPC61543
0.8554	High Similarity	NPC270768
0.8554	High Similarity	NPC225585
0.8554	High Similarity	NPC59263
0.8553	High Similarity	NPC246445
0.8553	High Similarity	NPC180886
0.8553	High Similarity	NPC899
0.8519	High Similarity	NPC29447
0.85	High Similarity	NPC215893
0.85	High Similarity	NPC69279
0.85	High Similarity	NPC53733
0.85	High Similarity	NPC307258
0.85	High Similarity	NPC83569
0.8481	Intermediate Similarity	NPC327002
0.8481	Intermediate Similarity	NPC477372
0.8462	Intermediate Similarity	NPC215843
0.8462	Intermediate Similarity	NPC192744
0.8452	Intermediate Similarity	NPC477872
0.8452	Intermediate Similarity	NPC130278
0.8452	Intermediate Similarity	NPC477288
0.8452	Intermediate Similarity	NPC46441
0.8452	Intermediate Similarity	NPC210037
0.8452	Intermediate Similarity	NPC7260
0.8452	Intermediate Similarity	NPC126369
0.8452	Intermediate Similarity	NPC193750
0.8452	Intermediate Similarity	NPC120840
0.8452	Intermediate Similarity	NPC111110
0.8452	Intermediate Similarity	NPC273621
0.8452	Intermediate Similarity	NPC86372
0.8452	Intermediate Similarity	NPC227467
0.8452	Intermediate Similarity	NPC474728
0.8452	Intermediate Similarity	NPC474964
0.8452	Intermediate Similarity	NPC172361
0.8452	Intermediate Similarity	NPC120968
0.8452	Intermediate Similarity	NPC290614
0.8452	Intermediate Similarity	NPC291028
0.8452	Intermediate Similarity	NPC18872
0.8452	Intermediate Similarity	NPC470589
0.8452	Intermediate Similarity	NPC113989
0.8452	Intermediate Similarity	NPC198818
0.8442	Intermediate Similarity	NPC61952
0.8442	Intermediate Similarity	NPC66105
0.8442	Intermediate Similarity	NPC472300
0.8415	Intermediate Similarity	NPC155011
0.8415	Intermediate Similarity	NPC73038
0.8415	Intermediate Similarity	NPC325594
0.84	Intermediate Similarity	NPC35656
0.8395	Intermediate Similarity	NPC171789
0.8395	Intermediate Similarity	NPC180834
0.8395	Intermediate Similarity	NPC248758
0.8395	Intermediate Similarity	NPC312660
0.8378	Intermediate Similarity	NPC91369
0.8375	Intermediate Similarity	NPC302661
0.8375	Intermediate Similarity	NPC133391
0.8375	Intermediate Similarity	NPC238991
0.8354	Intermediate Similarity	NPC2482
0.8353	Intermediate Similarity	NPC60755
0.8353	Intermediate Similarity	NPC105189
0.8353	Intermediate Similarity	NPC476064
0.8353	Intermediate Similarity	NPC71074
0.8353	Intermediate Similarity	NPC228784
0.8353	Intermediate Similarity	NPC285184
0.8353	Intermediate Similarity	NPC158030
0.8353	Intermediate Similarity	NPC25299
0.8353	Intermediate Similarity	NPC65120
0.8353	Intermediate Similarity	NPC300351
0.8353	Intermediate Similarity	NPC77099
0.8353	Intermediate Similarity	NPC471588
0.8353	Intermediate Similarity	NPC84319
0.8353	Intermediate Similarity	NPC230064
0.8353	Intermediate Similarity	NPC145067
0.8353	Intermediate Similarity	NPC472149
0.8353	Intermediate Similarity	NPC235884
0.8353	Intermediate Similarity	NPC38754
0.8353	Intermediate Similarity	NPC155120
0.8353	Intermediate Similarity	NPC324341
0.8353	Intermediate Similarity	NPC187722
0.8353	Intermediate Similarity	NPC306541
0.8353	Intermediate Similarity	NPC474525
0.8353	Intermediate Similarity	NPC966

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 NPC471897 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1670
0.2-0.3	3997
0.3-0.4	2204
0.4-0.5	630
0.5-0.6	244
0.6-0.7	163
0.7-0.8	59
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8353	Intermediate Similarity	NPD7515	Phase 2
0.8333	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7748	Approved
0.8	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4786	Approved
0.7927	Intermediate Similarity	NPD3667	Approved
0.7927	Intermediate Similarity	NPD4223	Phase 3
0.7927	Intermediate Similarity	NPD4221	Approved
0.7901	Intermediate Similarity	NPD4695	Discontinued
0.7889	Intermediate Similarity	NPD7902	Approved
0.7857	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5329	Approved
0.7841	Intermediate Similarity	NPD6399	Phase 3
0.7778	Intermediate Similarity	NPD7614	Phase 1
0.7765	Intermediate Similarity	NPD5330	Approved
0.7765	Intermediate Similarity	NPD6098	Approved
0.7765	Intermediate Similarity	NPD7521	Approved
0.7765	Intermediate Similarity	NPD7334	Approved
0.7765	Intermediate Similarity	NPD6684	Approved
0.7765	Intermediate Similarity	NPD6409	Approved
0.7765	Intermediate Similarity	NPD7146	Approved
0.7738	Intermediate Similarity	NPD4197	Approved
0.7738	Intermediate Similarity	NPD3665	Phase 1
0.7738	Intermediate Similarity	NPD3666	Approved
0.7738	Intermediate Similarity	NPD3133	Approved
0.7674	Intermediate Similarity	NPD3573	Approved
0.7654	Intermediate Similarity	NPD3617	Approved
0.7586	Intermediate Similarity	NPD5737	Approved
0.7586	Intermediate Similarity	NPD6672	Approved
0.7586	Intermediate Similarity	NPD6903	Approved
0.7558	Intermediate Similarity	NPD4688	Approved
0.7558	Intermediate Similarity	NPD4138	Approved
0.7558	Intermediate Similarity	NPD4690	Approved
0.7558	Intermediate Similarity	NPD4689	Approved
0.7558	Intermediate Similarity	NPD3618	Phase 1
0.7558	Intermediate Similarity	NPD4623	Approved
0.7558	Intermediate Similarity	NPD4693	Phase 3
0.7558	Intermediate Similarity	NPD4519	Discontinued
0.7558	Intermediate Similarity	NPD5205	Approved
0.7556	Intermediate Similarity	NPD7900	Approved
0.7556	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD5284	Approved
0.7528	Intermediate Similarity	NPD5281	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7386	Intermediate Similarity	NPD5208	Approved
0.7368	Intermediate Similarity	NPD4224	Phase 2
0.7356	Intermediate Similarity	NPD5690	Phase 2
0.7356	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5280	Approved
0.7356	Intermediate Similarity	NPD4694	Approved
0.7349	Intermediate Similarity	NPD7645	Phase 2
0.7342	Intermediate Similarity	NPD4243	Approved
0.7333	Intermediate Similarity	NPD6079	Approved
0.7333	Intermediate Similarity	NPD8035	Phase 2
0.7333	Intermediate Similarity	NPD8034	Phase 2
0.7326	Intermediate Similarity	NPD3668	Phase 3
0.7308	Intermediate Similarity	NPD4137	Phase 3
0.7303	Intermediate Similarity	NPD4753	Phase 2
0.7294	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5695	Phase 3
0.7234	Intermediate Similarity	NPD5696	Approved
0.7215	Intermediate Similarity	NPD4691	Approved
0.7215	Intermediate Similarity	NPD4747	Approved
0.7209	Intermediate Similarity	NPD4788	Approved
0.7204	Intermediate Similarity	NPD7732	Phase 3
0.7179	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4139	Approved
0.7176	Intermediate Similarity	NPD4692	Approved
0.716	Intermediate Similarity	NPD4784	Approved
0.716	Intermediate Similarity	NPD4785	Approved
0.7159	Intermediate Similarity	NPD5279	Phase 3
0.7158	Intermediate Similarity	NPD6404	Discontinued
0.7143	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD4195	Approved
0.7143	Intermediate Similarity	NPD6050	Approved
0.7143	Intermediate Similarity	NPD5693	Phase 1
0.7125	Intermediate Similarity	NPD6081	Approved
0.7097	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6942	Approved
0.7073	Intermediate Similarity	NPD7339	Approved
0.7065	Intermediate Similarity	NPD4202	Approved
0.7053	Intermediate Similarity	NPD7638	Approved
0.7033	Intermediate Similarity	NPD5207	Approved
0.7033	Intermediate Similarity	NPD5692	Phase 3
0.6989	Remote Similarity	NPD6001	Approved
0.6988	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7640	Approved
0.6979	Remote Similarity	NPD7639	Approved
0.697	Remote Similarity	NPD6402	Approved
0.697	Remote Similarity	NPD5739	Approved
0.697	Remote Similarity	NPD7128	Approved
0.697	Remote Similarity	NPD6675	Approved
0.6957	Remote Similarity	NPD5694	Approved
0.6951	Remote Similarity	NPD4058	Approved
0.6951	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5733	Approved
0.6923	Remote Similarity	NPD7331	Phase 2
0.6923	Remote Similarity	NPD6101	Approved
0.6923	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4629	Approved
0.6915	Remote Similarity	NPD5210	Approved
0.6867	Remote Similarity	NPD4190	Phase 3
0.6867	Remote Similarity	NPD5275	Approved
0.6867	Remote Similarity	NPD8039	Approved
0.686	Remote Similarity	NPD7525	Registered
0.6848	Remote Similarity	NPD4096	Approved
0.6842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5222	Approved
0.6842	Remote Similarity	NPD5221	Approved
0.6842	Remote Similarity	NPD4697	Phase 3
0.6832	Remote Similarity	NPD6881	Approved
0.6832	Remote Similarity	NPD6899	Approved
0.6832	Remote Similarity	NPD7320	Approved
0.6806	Remote Similarity	NPD3194	Approved
0.6806	Remote Similarity	NPD3195	Phase 2
0.6806	Remote Similarity	NPD4266	Approved
0.6806	Remote Similarity	NPD3196	Approved
0.6795	Remote Similarity	NPD7341	Phase 2
0.6786	Remote Similarity	NPD6117	Approved
0.6782	Remote Similarity	NPD8028	Phase 2
0.6771	Remote Similarity	NPD4755	Approved
0.6771	Remote Similarity	NPD5173	Approved
0.6765	Remote Similarity	NPD6373	Approved
0.6765	Remote Similarity	NPD6372	Approved
0.675	Remote Similarity	NPD5360	Phase 3
0.675	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4687	Approved
0.6733	Remote Similarity	NPD5701	Approved
0.6733	Remote Similarity	NPD5697	Approved
0.6733	Remote Similarity	NPD6412	Phase 2
0.6707	Remote Similarity	NPD5276	Approved
0.6706	Remote Similarity	NPD6116	Phase 1
0.6702	Remote Similarity	NPD5133	Approved
0.6699	Remote Similarity	NPD6883	Approved
0.6699	Remote Similarity	NPD7290	Approved
0.6699	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD3172	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6635	Remote Similarity	NPD6650	Approved
0.6635	Remote Similarity	NPD8130	Phase 1
0.6635	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6617	Approved
0.6635	Remote Similarity	NPD6869	Approved
0.6635	Remote Similarity	NPD6649	Approved
0.6635	Remote Similarity	NPD6847	Approved
0.6633	Remote Similarity	NPD4696	Approved
0.6633	Remote Similarity	NPD5285	Approved
0.6633	Remote Similarity	NPD5286	Approved
0.6633	Remote Similarity	NPD4700	Approved
0.663	Remote Similarity	NPD4518	Approved
0.6628	Remote Similarity	NPD6114	Approved
0.6628	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6697	Approved
0.6628	Remote Similarity	NPD6118	Approved
0.6628	Remote Similarity	NPD6115	Approved
0.6602	Remote Similarity	NPD6012	Approved
0.6602	Remote Similarity	NPD6014	Approved
0.6602	Remote Similarity	NPD6013	Approved
0.66	Remote Similarity	NPD6052	Approved
0.6591	Remote Similarity	NPD857	Phase 3
0.6585	Remote Similarity	NPD4789	Approved
0.6585	Remote Similarity	NPD4245	Approved
0.6585	Remote Similarity	NPD4244	Approved
0.6571	Remote Similarity	NPD8297	Approved
0.6571	Remote Similarity	NPD6882	Approved
0.6566	Remote Similarity	NPD5223	Approved
0.6562	Remote Similarity	NPD5654	Approved
0.6559	Remote Similarity	NPD6051	Approved
0.6548	Remote Similarity	NPD6926	Approved
0.6548	Remote Similarity	NPD6924	Approved
0.6526	Remote Similarity	NPD5778	Approved
0.6526	Remote Similarity	NPD5779	Approved
0.6506	Remote Similarity	NPD5777	Approved
0.6506	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6686	Approved
0.65	Remote Similarity	NPD5091	Approved
0.65	Remote Similarity	NPD5225	Approved
0.65	Remote Similarity	NPD5226	Approved
0.65	Remote Similarity	NPD4633	Approved
0.65	Remote Similarity	NPD5224	Approved
0.65	Remote Similarity	NPD5211	Phase 2
0.6484	Remote Similarity	NPD1694	Approved
0.6481	Remote Similarity	NPD7115	Discovery
0.6471	Remote Similarity	NPD3702	Approved
0.6463	Remote Similarity	NPD3698	Phase 2
0.6463	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4754	Approved
0.6436	Remote Similarity	NPD5174	Approved
0.6436	Remote Similarity	NPD5175	Approved
0.6429	Remote Similarity	NPD5959	Approved
0.6408	Remote Similarity	NPD6614	Approved
0.6395	Remote Similarity	NPD6933	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