NPASS Compound

Structure

NPC9674 OpenBabel07101719242D 27 31 0 0 1 0 0 0 0 0999 V2000 3.3584 -3.1020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9650 0.5987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8644 -3.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9756 -1.4943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1557 -2.9702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8105 -0.5263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2574 -2.1409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4386 -0.2118 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9067 -2.3620 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5825 -0.6114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8000 -0.8065 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4855 -0.9142 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2517 -0.1235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4205 -1.6577 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8286 -1.5173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4047 -1.5104 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6548 -2.4438 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5604 -1.4598 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7510 -0.6082 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0657 0.2255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0349 -0.1192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5571 0.7933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7928 -1.4512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7106 -0.7227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5710 -2.1617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6214 -0.7124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 17 1 0 0 0 0 6 25 1 0 0 0 0 8 2 1 1 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 18 1 1 0 0 0 9 26 1 0 0 0 0 10 20 2 0 0 0 0 10 27 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 1 0 0 0 12 15 1 0 0 0 0 12 21 1 6 0 0 0 13 19 1 1 0 0 0 13 22 1 0 0 0 0 14 7 1 1 0 0 0 14 17 1 0 0 0 0 14 27 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 17 1 6 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 3 1 6 0 0 0 18 6 1 6 0 0 0 19 24 1 6 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.15
Volume:	356.81
LogP:	1.427
LogD:	0.5
LogS:	-2.818
# Rotatable Bonds:	1
TPSA:	129.59
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.508
Synthetic Accessibility Score:	6.706
Fsp3:	0.737
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.864
MDCK Permeability:	1.5010459719633218e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.856

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.206
Plasma Protein Binding (PPB):	77.84825897216797%
Volume Distribution (VD):	0.871
Pgp-substrate:	28.17547035217285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.348
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.086
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.137
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	3.314
Half-life (T1/2):	0.576

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.477
Drug-inuced Liver Injury (DILI):	0.806
AMES Toxicity:	0.193
Rat Oral Acute Toxicity:	0.661
Maximum Recommended Daily Dose:	0.318
Skin Sensitization:	0.089
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC9674

Natural Product ID:	NPC9674
*Common Name:**	Polyandrol
IUPAC Name:	n.a.
Synonyms:	Polyandrol
Standard InCHIKey:	IRGXOUHTTCDCTK-ZTJWCXPSSA-N
Standard InCHI:	InChI=1S/C19H24O8/c1-7-4-10(20)27-14(7)17(3)5-9-18-6-25-19(24,16(17)18)13(22)8(2)11(18)12(21)15(23)26-9/h4,8-9,11-14,16,21-22,24H,5-6H2,1-3H3/t8-,9-,11-,12-,13-,14+,16-,17-,18+,19+/m1/s1
SMILES:	CC1=CC(=O)O[C@@H]1[C@@]1(C)C[C@@H]2[C@@]34CO[C@@]([C@@H]([C@H](C)[C@@H]3[C@H](C(=O)O2)O)O)([C@H]14)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479905
PubChem CID:	44575526
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO22346	Simaba cedron	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644063]
NPO22346	Simaba cedron	Species	Simaroubaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	17.0	ug.mL-1	PMID[536432]

☑ 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 NPC9674 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	247
0.1-0.2	1388
0.2-0.3	4468
0.3-0.4	8037
0.4-0.5	12799
0.5-0.6	6444
0.6-0.7	6560
0.7-0.8	2545
0.8-0.85	191
0.85-0.9	11
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC19028
0.9725	High Similarity	NPC106228
0.9725	High Similarity	NPC138372
0.9633	High Similarity	NPC178289
0.9211	High Similarity	NPC472004
0.8852	High Similarity	NPC88668
0.8814	High Similarity	NPC27363
0.8667	High Similarity	NPC250556
0.8667	High Similarity	NPC469750
0.8632	High Similarity	NPC475775
0.8632	High Similarity	NPC476529
0.8629	High Similarity	NPC471234
0.8595	High Similarity	NPC240070
0.8595	High Similarity	NPC117702
0.8595	High Similarity	NPC471356
0.8595	High Similarity	NPC179412
0.8595	High Similarity	NPC471357
0.8595	High Similarity	NPC329784
0.8595	High Similarity	NPC146456
0.8595	High Similarity	NPC469757
0.8559	High Similarity	NPC109607
0.8559	High Similarity	NPC107338
0.8537	High Similarity	NPC159338
0.8537	High Similarity	NPC253456
0.8537	High Similarity	NPC16569
0.8525	High Similarity	NPC311534
0.85	High Similarity	NPC469382
0.8475	Intermediate Similarity	NPC469380
0.8468	Intermediate Similarity	NPC471855
0.8468	Intermediate Similarity	NPC42670
0.8468	Intermediate Similarity	NPC19124
0.8468	Intermediate Similarity	NPC93416
0.8462	Intermediate Similarity	NPC473968
0.8455	Intermediate Similarity	NPC9499
0.8455	Intermediate Similarity	NPC86159
0.8455	Intermediate Similarity	NPC329986
0.8455	Intermediate Similarity	NPC180079
0.8455	Intermediate Similarity	NPC471358
0.8455	Intermediate Similarity	NPC91
0.8455	Intermediate Similarity	NPC89514
0.8455	Intermediate Similarity	NPC471361
0.8455	Intermediate Similarity	NPC471360
0.8455	Intermediate Similarity	NPC469753
0.8455	Intermediate Similarity	NPC469751
0.8455	Intermediate Similarity	NPC469754
0.8455	Intermediate Similarity	NPC10823
0.8455	Intermediate Similarity	NPC284406
0.8455	Intermediate Similarity	NPC276838
0.8455	Intermediate Similarity	NPC125077
0.8455	Intermediate Similarity	NPC471359
0.8455	Intermediate Similarity	NPC17896
0.8455	Intermediate Similarity	NPC140092
0.8455	Intermediate Similarity	NPC251866
0.8455	Intermediate Similarity	NPC219085
0.8455	Intermediate Similarity	NPC70542
0.8455	Intermediate Similarity	NPC6108
0.8455	Intermediate Similarity	NPC232785
0.8455	Intermediate Similarity	NPC471352
0.8455	Intermediate Similarity	NPC469755
0.8455	Intermediate Similarity	NPC197707
0.8455	Intermediate Similarity	NPC188234
0.8455	Intermediate Similarity	NPC469752
0.8435	Intermediate Similarity	NPC11252
0.8435	Intermediate Similarity	NPC302146
0.8435	Intermediate Similarity	NPC289312
0.843	Intermediate Similarity	NPC86346
0.843	Intermediate Similarity	NPC469379
0.843	Intermediate Similarity	NPC75856
0.8417	Intermediate Similarity	NPC222688
0.8403	Intermediate Similarity	NPC470312
0.8403	Intermediate Similarity	NPC109973
0.84	Intermediate Similarity	NPC477709
0.84	Intermediate Similarity	NPC298783
0.84	Intermediate Similarity	NPC104585
0.84	Intermediate Similarity	NPC225385
0.84	Intermediate Similarity	NPC157817
0.84	Intermediate Similarity	NPC476221
0.8376	Intermediate Similarity	NPC266728
0.8376	Intermediate Similarity	NPC49492
0.8376	Intermediate Similarity	NPC196931
0.8362	Intermediate Similarity	NPC194100
0.8362	Intermediate Similarity	NPC51978
0.8348	Intermediate Similarity	NPC201992
0.8347	Intermediate Similarity	NPC471392
0.8333	Intermediate Similarity	NPC471999
0.8333	Intermediate Similarity	NPC472000
0.8306	Intermediate Similarity	NPC471407
0.8306	Intermediate Similarity	NPC470851
0.8305	Intermediate Similarity	NPC152615
0.8291	Intermediate Similarity	NPC469877
0.8291	Intermediate Similarity	NPC474906
0.8291	Intermediate Similarity	NPC18547
0.8291	Intermediate Similarity	NPC470919
0.8279	Intermediate Similarity	NPC470922
0.8268	Intermediate Similarity	NPC171619
0.8261	Intermediate Similarity	NPC475563
0.8261	Intermediate Similarity	NPC206595
0.8261	Intermediate Similarity	NPC475134
0.8254	Intermediate Similarity	NPC116075
0.8254	Intermediate Similarity	NPC469749
0.8254	Intermediate Similarity	NPC32793
0.8254	Intermediate Similarity	NPC142756
0.8254	Intermediate Similarity	NPC247190
0.8254	Intermediate Similarity	NPC146857
0.825	Intermediate Similarity	NPC143755
0.824	Intermediate Similarity	NPC473838
0.824	Intermediate Similarity	NPC475389
0.8226	Intermediate Similarity	NPC470850
0.8226	Intermediate Similarity	NPC473888
0.822	Intermediate Similarity	NPC5311
0.822	Intermediate Similarity	NPC99620
0.822	Intermediate Similarity	NPC471816
0.822	Intermediate Similarity	NPC474046
0.822	Intermediate Similarity	NPC235539
0.822	Intermediate Similarity	NPC310341
0.822	Intermediate Similarity	NPC134869
0.822	Intermediate Similarity	NPC193382
0.822	Intermediate Similarity	NPC259306
0.822	Intermediate Similarity	NPC152199
0.822	Intermediate Similarity	NPC470628
0.822	Intermediate Similarity	NPC199428
0.8205	Intermediate Similarity	NPC962
0.8205	Intermediate Similarity	NPC250109
0.8197	Intermediate Similarity	NPC473979
0.8197	Intermediate Similarity	NPC129992
0.819	Intermediate Similarity	NPC475668
0.819	Intermediate Similarity	NPC473921
0.819	Intermediate Similarity	NPC475480
0.8189	Intermediate Similarity	NPC329636
0.8174	Intermediate Similarity	NPC143706
0.8174	Intermediate Similarity	NPC472534
0.8174	Intermediate Similarity	NPC257853
0.8167	Intermediate Similarity	NPC475041
0.8167	Intermediate Similarity	NPC329905
0.816	Intermediate Similarity	NPC104382
0.816	Intermediate Similarity	NPC231529
0.816	Intermediate Similarity	NPC472770
0.816	Intermediate Similarity	NPC175186
0.8151	Intermediate Similarity	NPC471351
0.8151	Intermediate Similarity	NPC243196
0.8151	Intermediate Similarity	NPC203862
0.8151	Intermediate Similarity	NPC471355
0.8151	Intermediate Similarity	NPC471354
0.8151	Intermediate Similarity	NPC474418
0.8151	Intermediate Similarity	NPC196429
0.8151	Intermediate Similarity	NPC77319
0.8151	Intermediate Similarity	NPC473590
0.8151	Intermediate Similarity	NPC284068
0.8151	Intermediate Similarity	NPC84987
0.8151	Intermediate Similarity	NPC34390
0.8151	Intermediate Similarity	NPC27507
0.8151	Intermediate Similarity	NPC244402
0.8151	Intermediate Similarity	NPC309034
0.8151	Intermediate Similarity	NPC99728
0.8151	Intermediate Similarity	NPC470171
0.8151	Intermediate Similarity	NPC50305
0.8151	Intermediate Similarity	NPC87250
0.8151	Intermediate Similarity	NPC93883
0.8151	Intermediate Similarity	NPC471353
0.8151	Intermediate Similarity	NPC142066
0.8151	Intermediate Similarity	NPC157376
0.8151	Intermediate Similarity	NPC158344
0.8151	Intermediate Similarity	NPC473852
0.8145	Intermediate Similarity	NPC287423
0.8145	Intermediate Similarity	NPC476008
0.8145	Intermediate Similarity	NPC470882
0.8136	Intermediate Similarity	NPC31354
0.8136	Intermediate Similarity	NPC69576
0.8136	Intermediate Similarity	NPC84949
0.8136	Intermediate Similarity	NPC90472
0.8136	Intermediate Similarity	NPC326542
0.8136	Intermediate Similarity	NPC471633
0.8125	Intermediate Similarity	NPC295791
0.8125	Intermediate Similarity	NPC194716
0.812	Intermediate Similarity	NPC126691
0.812	Intermediate Similarity	NPC207251
0.8115	Intermediate Similarity	NPC312833
0.8115	Intermediate Similarity	NPC28532
0.8115	Intermediate Similarity	NPC269642
0.8103	Intermediate Similarity	NPC179642
0.8103	Intermediate Similarity	NPC472666
0.8103	Intermediate Similarity	NPC5103
0.8099	Intermediate Similarity	NPC474585
0.8099	Intermediate Similarity	NPC474466
0.8099	Intermediate Similarity	NPC112038
0.8099	Intermediate Similarity	NPC151616
0.8099	Intermediate Similarity	NPC4548
0.8099	Intermediate Similarity	NPC475136
0.8095	Intermediate Similarity	NPC241935
0.8095	Intermediate Similarity	NPC471170
0.8095	Intermediate Similarity	NPC279478
0.8095	Intermediate Similarity	NPC173347
0.8087	Intermediate Similarity	NPC88701
0.8087	Intermediate Similarity	NPC293850
0.8083	Intermediate Similarity	NPC311554
0.8083	Intermediate Similarity	NPC297179
0.8083	Intermediate Similarity	NPC83287
0.8083	Intermediate Similarity	NPC188667
0.8083	Intermediate Similarity	NPC475372
0.8083	Intermediate Similarity	NPC257457

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 NPC9674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	1670
0.2-0.3	3852
0.3-0.4	2225
0.4-0.5	678
0.5-0.6	263
0.6-0.7	132
0.7-0.8	103
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD7507	Approved
0.8455	Intermediate Similarity	NPD7319	Approved
0.8167	Intermediate Similarity	NPD7516	Approved
0.8083	Intermediate Similarity	NPD7327	Approved
0.8083	Intermediate Similarity	NPD7328	Approved
0.8	Intermediate Similarity	NPD7078	Approved
0.7984	Intermediate Similarity	NPD7492	Approved
0.7951	Intermediate Similarity	NPD6054	Approved
0.7951	Intermediate Similarity	NPD8377	Approved
0.7951	Intermediate Similarity	NPD6319	Approved
0.7951	Intermediate Similarity	NPD8294	Approved
0.7951	Intermediate Similarity	NPD6059	Approved
0.7931	Intermediate Similarity	NPD6686	Approved
0.792	Intermediate Similarity	NPD6616	Approved
0.7899	Intermediate Similarity	NPD4632	Approved
0.7886	Intermediate Similarity	NPD8378	Approved
0.7886	Intermediate Similarity	NPD6016	Approved
0.7886	Intermediate Similarity	NPD8296	Approved
0.7886	Intermediate Similarity	NPD8380	Approved
0.7886	Intermediate Similarity	NPD6015	Approved
0.7886	Intermediate Similarity	NPD8379	Approved
0.7886	Intermediate Similarity	NPD8033	Approved
0.7886	Intermediate Similarity	NPD8335	Approved
0.7857	Intermediate Similarity	NPD8293	Discontinued
0.7851	Intermediate Similarity	NPD6009	Approved
0.7823	Intermediate Similarity	NPD5988	Approved
0.7823	Intermediate Similarity	NPD6370	Approved
0.7815	Intermediate Similarity	NPD8297	Approved
0.7815	Intermediate Similarity	NPD6882	Approved
0.7795	Intermediate Similarity	NPD7736	Approved
0.7778	Intermediate Similarity	NPD7320	Approved
0.7759	Intermediate Similarity	NPD6675	Approved
0.7759	Intermediate Similarity	NPD5739	Approved
0.7759	Intermediate Similarity	NPD7128	Approved
0.7759	Intermediate Similarity	NPD6402	Approved
0.7712	Intermediate Similarity	NPD6372	Approved
0.7712	Intermediate Similarity	NPD6373	Approved
0.7699	Intermediate Similarity	NPD7638	Approved
0.7692	Intermediate Similarity	NPD5697	Approved
0.7692	Intermediate Similarity	NPD5701	Approved
0.7632	Intermediate Similarity	NPD7640	Approved
0.7632	Intermediate Similarity	NPD7639	Approved
0.7627	Intermediate Similarity	NPD6899	Approved
0.7627	Intermediate Similarity	NPD6881	Approved
0.7583	Intermediate Similarity	NPD6650	Approved
0.7583	Intermediate Similarity	NPD6649	Approved
0.7563	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD6013	Approved
0.7563	Intermediate Similarity	NPD6012	Approved
0.7563	Intermediate Similarity	NPD6014	Approved
0.7542	Intermediate Similarity	NPD6412	Phase 2
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.7479	Intermediate Similarity	NPD6011	Approved
0.746	Intermediate Similarity	NPD7503	Approved
0.746	Intermediate Similarity	NPD5983	Phase 2
0.7458	Intermediate Similarity	NPD6008	Approved
0.7456	Intermediate Similarity	NPD4755	Approved
0.7438	Intermediate Similarity	NPD6617	Approved
0.7438	Intermediate Similarity	NPD6869	Approved
0.7438	Intermediate Similarity	NPD6847	Approved
0.7438	Intermediate Similarity	NPD8130	Phase 1
0.7385	Intermediate Similarity	NPD6033	Approved
0.7377	Intermediate Similarity	NPD6053	Discontinued
0.7355	Intermediate Similarity	NPD4634	Approved
0.7355	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD5211	Phase 2
0.7344	Intermediate Similarity	NPD7604	Phase 2
0.7344	Intermediate Similarity	NPD8328	Phase 3
0.7333	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5285	Approved
0.7328	Intermediate Similarity	NPD5286	Approved
0.7328	Intermediate Similarity	NPD4700	Approved
0.7328	Intermediate Similarity	NPD4696	Approved
0.7317	Intermediate Similarity	NPD8133	Approved
0.7295	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4225	Approved
0.7231	Intermediate Similarity	NPD6336	Discontinued
0.7227	Intermediate Similarity	NPD5141	Approved
0.7203	Intermediate Similarity	NPD5224	Approved
0.7203	Intermediate Similarity	NPD5225	Approved
0.7203	Intermediate Similarity	NPD4633	Approved
0.7203	Intermediate Similarity	NPD5226	Approved
0.72	Intermediate Similarity	NPD6274	Approved
0.7167	Intermediate Similarity	NPD4768	Approved
0.7167	Intermediate Similarity	NPD4767	Approved
0.7155	Intermediate Similarity	NPD6083	Phase 2
0.7155	Intermediate Similarity	NPD6084	Phase 2
0.7143	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD5174	Approved
0.713	Intermediate Similarity	NPD5695	Phase 3
0.7119	Intermediate Similarity	NPD5223	Approved
0.7107	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD46	Approved
0.708	Intermediate Similarity	NPD6698	Approved
0.7059	Intermediate Similarity	NPD7632	Discontinued
0.7054	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4729	Approved
0.7049	Intermediate Similarity	NPD4730	Approved
0.7031	Intermediate Similarity	NPD7100	Approved
0.7031	Intermediate Similarity	NPD7101	Approved
0.7008	Intermediate Similarity	NPD6317	Approved
0.7008	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4754	Approved
0.6992	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6335	Approved
0.6953	Remote Similarity	NPD6313	Approved
0.6953	Remote Similarity	NPD6314	Approved
0.6949	Remote Similarity	NPD5696	Approved
0.6947	Remote Similarity	NPD6067	Discontinued
0.6935	Remote Similarity	NPD5250	Approved
0.6935	Remote Similarity	NPD5247	Approved
0.6935	Remote Similarity	NPD5251	Approved
0.6935	Remote Similarity	NPD5248	Approved
0.6935	Remote Similarity	NPD5249	Phase 3
0.6923	Remote Similarity	NPD8513	Phase 3
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4697	Phase 3
0.6923	Remote Similarity	NPD5222	Approved
0.6923	Remote Similarity	NPD8516	Approved
0.6923	Remote Similarity	NPD5221	Approved
0.6923	Remote Similarity	NPD6908	Approved
0.6923	Remote Similarity	NPD8517	Approved
0.6923	Remote Similarity	NPD8515	Approved
0.6923	Remote Similarity	NPD6909	Approved
0.6911	Remote Similarity	NPD5128	Approved
0.688	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5693	Phase 1
0.6864	Remote Similarity	NPD5173	Approved
0.6842	Remote Similarity	NPD4753	Phase 2
0.6842	Remote Similarity	NPD5328	Approved
0.6838	Remote Similarity	NPD7260	Phase 2
0.6833	Remote Similarity	NPD1700	Approved
0.681	Remote Similarity	NPD4202	Approved
0.6803	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6371	Approved
0.6794	Remote Similarity	NPD6921	Approved
0.6788	Remote Similarity	NPD6845	Suspended
0.6765	Remote Similarity	NPD5956	Approved
0.6759	Remote Similarity	NPD7625	Phase 1
0.6746	Remote Similarity	NPD5215	Approved
0.6746	Remote Similarity	NPD5217	Approved
0.6746	Remote Similarity	NPD5216	Approved
0.6724	Remote Similarity	NPD6079	Approved
0.6695	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD6334	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6333	Approved
0.6614	Remote Similarity	NPD5127	Approved
0.6609	Remote Similarity	NPD6672	Approved
0.6609	Remote Similarity	NPD6903	Approved
0.6609	Remote Similarity	NPD5737	Approved
0.6579	Remote Similarity	NPD6684	Approved
0.6579	Remote Similarity	NPD7334	Approved
0.6579	Remote Similarity	NPD6409	Approved
0.6579	Remote Similarity	NPD7146	Approved
0.6579	Remote Similarity	NPD3618	Phase 1
0.6579	Remote Similarity	NPD5330	Approved
0.6579	Remote Similarity	NPD7521	Approved
0.6555	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5210	Approved
0.6555	Remote Similarity	NPD4629	Approved
0.6552	Remote Similarity	NPD6904	Approved
0.6552	Remote Similarity	NPD6673	Approved
0.6552	Remote Similarity	NPD6080	Approved
0.6549	Remote Similarity	NPD3665	Phase 1
0.6549	Remote Similarity	NPD3133	Approved
0.6549	Remote Similarity	NPD3666	Approved
0.6496	Remote Similarity	NPD5692	Phase 3
0.6491	Remote Similarity	NPD1694	Approved
0.6479	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7748	Approved
0.6471	Remote Similarity	NPD6001	Approved
0.6471	Remote Similarity	NPD5282	Discontinued
0.6466	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5167	Approved
0.6446	Remote Similarity	NPD7902	Approved
0.6441	Remote Similarity	NPD7983	Approved
0.6441	Remote Similarity	NPD8035	Phase 2
0.6441	Remote Similarity	NPD5284	Approved
0.6441	Remote Similarity	NPD7515	Phase 2
0.6441	Remote Similarity	NPD5694	Approved
0.6441	Remote Similarity	NPD6050	Approved
0.6441	Remote Similarity	NPD5281	Approved
0.6441	Remote Similarity	NPD8034	Phase 2
0.6435	Remote Similarity	NPD4249	Approved
0.6435	Remote Similarity	NPD5279	Phase 3
0.642	Remote Similarity	NPD7799	Discontinued
0.6404	Remote Similarity	NPD4197	Approved
0.6393	Remote Similarity	NPD8029	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data