NPASS Compound

Structure

CID131903 OpenBabel06191715492D 32 36 0 0 1 0 0 0 0 0999 V2000 2.9111 -1.9534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2313 2.5213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3640 -2.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1779 0.4209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7928 -3.2038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -2.7461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9115 -1.6630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3133 -2.0926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5855 -1.8307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0327 0.1800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7927 -0.4577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0432 -1.9534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4501 1.6606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4748 -1.1195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5855 -2.7461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.8307 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9486 -0.9274 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6713 -0.5674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7081 -1.3730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0343 -0.1600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3966 -0.4399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7927 -1.3731 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7928 -1.3730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7927 -0.4577 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3049 1.4196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2934 -0.7749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1420 -0.6214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0321 0.7256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6762 -0.3665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8140 1.0407 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 -2.7671 -0.5829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 5 6 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 9 15 1 0 0 0 0 9 23 1 0 0 0 0 10 21 1 0 0 0 0 10 30 1 0 0 0 0 11 22 1 0 0 0 0 11 31 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 25 2 0 0 0 0 13 30 1 0 0 0 0 14 26 2 0 0 0 0 14 32 1 0 0 0 0 15 5 1 6 0 0 0 16 22 1 1 0 0 0 16 23 1 0 0 0 0 17 21 1 6 0 0 0 17 32 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 1 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 27 2 0 0 0 0 20 24 1 6 0 0 0 20 28 1 0 0 0 0 21 4 1 6 0 0 0 22 8 1 6 0 0 0 23 24 1 1 0 0 0 24 29 1 1 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.21
Volume:	440.654
LogP:	1.251
LogD:	1.029
LogS:	-3.886
# Rotatable Bonds:	5
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	6.83
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.119
MDCK Permeability:	5.498767495737411e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.815
30% Bioavailability (F30%):	0.899

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.669
Plasma Protein Binding (PPB):	59.74281311035156%
Volume Distribution (VD):	1.369
Pgp-substrate:	53.46211624145508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.306
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.506
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	2.104
Half-life (T1/2):	0.578

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.46
AMES Toxicity:	0.386
Rat Oral Acute Toxicity:	0.484
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.667
Carcinogencity:	0.629
Eye Corrosion:	0.004
Eye Irritation:	0.056
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC131903

Natural Product ID:	NPC131903
*Common Name:**	Maoecrystal J
IUPAC Name:	n.a.
Synonyms:	Maoecrystal J
Standard InCHIKey:	SLUROFCVEYCYDJ-MIWKWXCYSA-N
Standard InCHI:	InChI=1S/C24H32O8/c1-12-15-5-6-16-22-8-7-17(32-14(3)26)21(4,10-30-13(2)25)18(22)20(28)24(29,31-11-22)23(16,9-15)19(12)27/h15-18,20,28-29H,1,5-11H2,2-4H3/t15-,16+,17+,18-,20+,21-,22-,23+,24+/m1/s1
SMILES:	C=C1[C@@H]2CC[C@H]3[C@@]45CC[C@@H]([C@@](C)(COC(=O)C)[C@H]5[C@@H]([C@]([C@]3(C2)C1=O)(O)OC4)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641879
PubChem CID:	53317860
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO13742	Rabdosia macrophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14739	Rabdosia eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13742	Rabdosia macrophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14739	Rabdosia eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14739	Rabdosia eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13742	Rabdosia macrophylla	Species	Lamiaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	4200.0	nM	PMID[555272]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[555272]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	9800.0	nM	PMID[555272]

☑ 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 NPC131903 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	288
0.1-0.2	1957
0.2-0.3	6023
0.3-0.4	10890
0.4-0.5	9944
0.5-0.6	6040
0.6-0.7	4338
0.7-0.8	2289
0.8-0.85	752
0.85-0.9	106
0.9-0.95	35
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
0.9901	High Similarity	NPC137104
0.9901	High Similarity	NPC474786
0.9901	High Similarity	NPC320383
0.9802	High Similarity	NPC274827
0.9709	High Similarity	NPC474927
0.9706	High Similarity	NPC85391
0.9703	High Similarity	NPC471094
0.9703	High Similarity	NPC469984
0.9703	High Similarity	NPC473410
0.97	High Similarity	NPC56656
0.9612	High Similarity	NPC213320
0.9608	High Similarity	NPC102741
0.9604	High Similarity	NPC471474
0.9519	High Similarity	NPC473397
0.951	High Similarity	NPC63841
0.9505	High Similarity	NPC307660
0.9505	High Similarity	NPC130511
0.9434	High Similarity	NPC88945
0.9429	High Similarity	NPC132668
0.9429	High Similarity	NPC471252
0.9412	High Similarity	NPC186054
0.9333	High Similarity	NPC473352
0.9327	High Similarity	NPC471093
0.932	High Similarity	NPC189663
0.932	High Similarity	NPC89860
0.9245	High Similarity	NPC320118
0.9238	High Similarity	NPC29505
0.9231	High Similarity	NPC252679
0.9231	High Similarity	NPC118721
0.9223	High Similarity	NPC166993
0.9223	High Similarity	NPC67745
0.9223	High Similarity	NPC471461
0.9167	High Similarity	NPC473304
0.9151	High Similarity	NPC471244
0.9143	High Similarity	NPC471476
0.9135	High Similarity	NPC232133
0.9135	High Similarity	NPC273155
0.9135	High Similarity	NPC55973
0.9126	High Similarity	NPC138908
0.9126	High Similarity	NPC200957
0.9118	High Similarity	NPC209298
0.9118	High Similarity	NPC122811
0.9118	High Similarity	NPC139347
0.9118	High Similarity	NPC277074
0.9109	High Similarity	NPC14634
0.9074	High Similarity	NPC229752
0.9065	High Similarity	NPC194273
0.9065	High Similarity	NPC471248
0.9057	High Similarity	NPC63244
0.9048	High Similarity	NPC469983
0.9029	High Similarity	NPC301787
0.9029	High Similarity	NPC202793
0.8991	High Similarity	NPC78836
0.8981	High Similarity	NPC243354
0.8972	High Similarity	NPC145625
0.8972	High Similarity	NPC157929
0.8972	High Similarity	NPC471245
0.8962	High Similarity	NPC473324
0.8942	High Similarity	NPC222833
0.8922	High Similarity	NPC252614
0.8922	High Similarity	NPC236585
0.8911	High Similarity	NPC474793
0.8889	High Similarity	NPC94141
0.8889	High Similarity	NPC73986
0.8879	High Similarity	NPC56025
0.8879	High Similarity	NPC122339
0.8879	High Similarity	NPC471243
0.8835	High Similarity	NPC275990
0.8824	High Similarity	NPC470388
0.8807	High Similarity	NPC17165
0.8796	High Similarity	NPC207845
0.8796	High Similarity	NPC472719
0.8796	High Similarity	NPC473303
0.8774	High Similarity	NPC218123
0.8774	High Similarity	NPC112895
0.8774	High Similarity	NPC231278
0.875	High Similarity	NPC96217
0.8738	High Similarity	NPC46848
0.8725	High Similarity	NPC471038
0.8704	High Similarity	NPC274833
0.8704	High Similarity	NPC329953
0.8704	High Similarity	NPC11035
0.8692	High Similarity	NPC8431
0.8692	High Similarity	NPC469744
0.8679	High Similarity	NPC469746
0.8679	High Similarity	NPC88833
0.8679	High Similarity	NPC96333
0.8667	High Similarity	NPC474558
0.8654	High Similarity	NPC475803
0.8654	High Similarity	NPC309388
0.8654	High Similarity	NPC470172
0.8641	High Similarity	NPC287676
0.8624	High Similarity	NPC470543
0.8585	High Similarity	NPC4115
0.8571	High Similarity	NPC473406
0.8571	High Similarity	NPC87927
0.8559	High Similarity	NPC472718
0.8558	High Similarity	NPC52899
0.8558	High Similarity	NPC148279
0.8558	High Similarity	NPC289148
0.8558	High Similarity	NPC163963
0.8545	High Similarity	NPC146563
0.8544	High Similarity	NPC98837
0.8544	High Similarity	NPC78427
0.8544	High Similarity	NPC20479
0.8544	High Similarity	NPC38296
0.8544	High Similarity	NPC162459
0.8544	High Similarity	NPC16911
0.8544	High Similarity	NPC38471
0.8544	High Similarity	NPC28864
0.8532	High Similarity	NPC272242
0.8529	High Similarity	NPC200054
0.8529	High Similarity	NPC329910
0.8529	High Similarity	NPC29410
0.8519	High Similarity	NPC240125
0.8519	High Similarity	NPC51947
0.8519	High Similarity	NPC91583
0.8519	High Similarity	NPC473844
0.8515	High Similarity	NPC47853
0.8505	High Similarity	NPC61071
0.8505	High Similarity	NPC201908
0.8505	High Similarity	NPC176949
0.8491	Intermediate Similarity	NPC101842
0.8482	Intermediate Similarity	NPC470171
0.8482	Intermediate Similarity	NPC218970
0.8476	Intermediate Similarity	NPC148628
0.8476	Intermediate Similarity	NPC76866
0.8476	Intermediate Similarity	NPC286519
0.8476	Intermediate Similarity	NPC471254
0.8476	Intermediate Similarity	NPC88203
0.8476	Intermediate Similarity	NPC304832
0.8476	Intermediate Similarity	NPC214946
0.8476	Intermediate Similarity	NPC246736
0.8468	Intermediate Similarity	NPC54395
0.8462	Intermediate Similarity	NPC267921
0.8462	Intermediate Similarity	NPC293866
0.8455	Intermediate Similarity	NPC205534
0.8455	Intermediate Similarity	NPC243572
0.844	Intermediate Similarity	NPC100908
0.844	Intermediate Similarity	NPC49730
0.844	Intermediate Similarity	NPC98069
0.8431	Intermediate Similarity	NPC470232
0.8431	Intermediate Similarity	NPC98639
0.8431	Intermediate Similarity	NPC470229
0.8426	Intermediate Similarity	NPC469733
0.8426	Intermediate Similarity	NPC88744
0.8426	Intermediate Similarity	NPC469729
0.8411	Intermediate Similarity	NPC164600
0.8411	Intermediate Similarity	NPC12823
0.8411	Intermediate Similarity	NPC103172
0.8407	Intermediate Similarity	NPC239293
0.8407	Intermediate Similarity	NPC297179
0.8396	Intermediate Similarity	NPC471253
0.8393	Intermediate Similarity	NPC469820
0.8393	Intermediate Similarity	NPC137414
0.8393	Intermediate Similarity	NPC469823
0.8381	Intermediate Similarity	NPC471790
0.8378	Intermediate Similarity	NPC102619
0.8365	Intermediate Similarity	NPC26270
0.8365	Intermediate Similarity	NPC89099
0.8365	Intermediate Similarity	NPC469725
0.8364	Intermediate Similarity	NPC250481
0.8364	Intermediate Similarity	NPC240734
0.8364	Intermediate Similarity	NPC285410
0.8364	Intermediate Similarity	NPC91838
0.8364	Intermediate Similarity	NPC204392
0.8364	Intermediate Similarity	NPC275668
0.8364	Intermediate Similarity	NPC263827
0.8364	Intermediate Similarity	NPC1876
0.8349	Intermediate Similarity	NPC218853
0.8348	Intermediate Similarity	NPC470478
0.8333	Intermediate Similarity	NPC475118
0.8333	Intermediate Similarity	NPC470386
0.8333	Intermediate Similarity	NPC470385
0.8319	Intermediate Similarity	NPC474483
0.8319	Intermediate Similarity	NPC477252
0.8319	Intermediate Similarity	NPC156651
0.8318	Intermediate Similarity	NPC98603
0.8318	Intermediate Similarity	NPC13149
0.8304	Intermediate Similarity	NPC18547
0.8304	Intermediate Similarity	NPC474906
0.8302	Intermediate Similarity	NPC94919
0.8291	Intermediate Similarity	NPC469841
0.8291	Intermediate Similarity	NPC469842
0.8288	Intermediate Similarity	NPC289312
0.8288	Intermediate Similarity	NPC476964
0.8288	Intermediate Similarity	NPC11252
0.8273	Intermediate Similarity	NPC474567
0.8269	Intermediate Similarity	NPC96839
0.8269	Intermediate Similarity	NPC10864
0.8261	Intermediate Similarity	NPC476961
0.8261	Intermediate Similarity	NPC281840
0.8257	Intermediate Similarity	NPC224414
0.8252	Intermediate Similarity	NPC210214
0.8246	Intermediate Similarity	NPC188667
0.8246	Intermediate Similarity	NPC204552
0.8246	Intermediate Similarity	NPC469822
0.8241	Intermediate Similarity	NPC295366
0.8235	Intermediate Similarity	NPC294263
0.823	Intermediate Similarity	NPC44170

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 NPC131903 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	2334
0.2-0.3	3952
0.3-0.4	1662
0.4-0.5	479
0.5-0.6	249
0.6-0.7	151
0.7-0.8	38
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8053	Intermediate Similarity	NPD8133	Approved
0.8051	Intermediate Similarity	NPD8328	Phase 3
0.8018	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD6319	Approved
0.7724	Intermediate Similarity	NPD7319	Approved
0.7686	Intermediate Similarity	NPD7492	Approved
0.7679	Intermediate Similarity	NPD6412	Phase 2
0.7647	Intermediate Similarity	NPD6054	Approved
0.7642	Intermediate Similarity	NPD7736	Approved
0.7623	Intermediate Similarity	NPD7507	Approved
0.7623	Intermediate Similarity	NPD6616	Approved
0.7619	Intermediate Similarity	NPD8035	Phase 2
0.7619	Intermediate Similarity	NPD8034	Phase 2
0.7611	Intermediate Similarity	NPD6686	Approved
0.7561	Intermediate Similarity	NPD7078	Approved
0.7542	Intermediate Similarity	NPD7115	Discovery
0.7521	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.7438	Intermediate Similarity	NPD6015	Approved
0.7438	Intermediate Similarity	NPD6016	Approved
0.7436	Intermediate Similarity	NPD4632	Approved
0.7419	Intermediate Similarity	NPD8293	Discontinued
0.7414	Intermediate Similarity	NPD6650	Approved
0.7414	Intermediate Similarity	NPD6649	Approved
0.7395	Intermediate Similarity	NPD6009	Approved
0.7391	Intermediate Similarity	NPD6372	Approved
0.7391	Intermediate Similarity	NPD6373	Approved
0.7379	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD5988	Approved
0.7345	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD6881	Approved
0.7304	Intermediate Similarity	NPD6899	Approved
0.7295	Intermediate Similarity	NPD6921	Approved
0.7281	Intermediate Similarity	NPD5739	Approved
0.7281	Intermediate Similarity	NPD6675	Approved
0.7281	Intermediate Similarity	NPD6402	Approved
0.7281	Intermediate Similarity	NPD7128	Approved
0.7273	Intermediate Similarity	NPD7516	Approved
0.7222	Intermediate Similarity	NPD6399	Phase 3
0.7217	Intermediate Similarity	NPD5697	Approved
0.7213	Intermediate Similarity	NPD8377	Approved
0.7213	Intermediate Similarity	NPD8294	Approved
0.719	Intermediate Similarity	NPD7328	Approved
0.719	Intermediate Similarity	NPD7327	Approved
0.7179	Intermediate Similarity	NPD4634	Approved
0.7179	Intermediate Similarity	NPD7102	Approved
0.7179	Intermediate Similarity	NPD7290	Approved
0.7179	Intermediate Similarity	NPD6883	Approved
0.7155	Intermediate Similarity	NPD7320	Approved
0.7154	Intermediate Similarity	NPD8378	Approved
0.7154	Intermediate Similarity	NPD8380	Approved
0.7154	Intermediate Similarity	NPD8335	Approved
0.7154	Intermediate Similarity	NPD8033	Approved
0.7154	Intermediate Similarity	NPD8379	Approved
0.7154	Intermediate Similarity	NPD8296	Approved
0.7119	Intermediate Similarity	NPD6617	Approved
0.7119	Intermediate Similarity	NPD6847	Approved
0.7119	Intermediate Similarity	NPD8130	Phase 1
0.7119	Intermediate Similarity	NPD6869	Approved
0.7117	Intermediate Similarity	NPD7902	Approved
0.7094	Intermediate Similarity	NPD6013	Approved
0.7094	Intermediate Similarity	NPD6012	Approved
0.7094	Intermediate Similarity	NPD6014	Approved
0.7094	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5701	Approved
0.7054	Intermediate Similarity	NPD4225	Approved
0.7054	Intermediate Similarity	NPD7638	Approved
0.704	Intermediate Similarity	NPD7604	Phase 2
0.7034	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5983	Phase 2
0.7016	Intermediate Similarity	NPD8515	Approved
0.7016	Intermediate Similarity	NPD8517	Approved
0.7016	Intermediate Similarity	NPD7503	Approved
0.7016	Intermediate Similarity	NPD8513	Phase 3
0.7016	Intermediate Similarity	NPD8516	Approved
0.7009	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.6991	Remote Similarity	NPD7640	Approved
0.6991	Remote Similarity	NPD7639	Approved
0.6983	Remote Similarity	NPD6008	Approved
0.6972	Remote Similarity	NPD6079	Approved
0.6972	Remote Similarity	NPD7515	Phase 2
0.6953	Remote Similarity	NPD6033	Approved
0.6944	Remote Similarity	NPD5328	Approved
0.6929	Remote Similarity	NPD6336	Discontinued
0.6863	Remote Similarity	NPD6115	Approved
0.6863	Remote Similarity	NPD6697	Approved
0.6863	Remote Similarity	NPD6118	Approved
0.6863	Remote Similarity	NPD6114	Approved
0.6847	Remote Similarity	NPD7900	Approved
0.6847	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5286	Approved
0.6842	Remote Similarity	NPD4696	Approved
0.6842	Remote Similarity	NPD5285	Approved
0.6833	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3618	Phase 1
0.6814	Remote Similarity	NPD6083	Phase 2
0.6814	Remote Similarity	NPD4755	Approved
0.6814	Remote Similarity	NPD6084	Phase 2
0.678	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6116	Phase 1
0.6748	Remote Similarity	NPD6274	Approved
0.6726	Remote Similarity	NPD5221	Approved
0.6726	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5222	Approved
0.6726	Remote Similarity	NPD4697	Phase 3
0.6724	Remote Similarity	NPD5226	Approved
0.6724	Remote Similarity	NPD5225	Approved
0.6724	Remote Similarity	NPD5224	Approved
0.6724	Remote Similarity	NPD4633	Approved
0.6724	Remote Similarity	NPD5211	Phase 2
0.672	Remote Similarity	NPD7101	Approved
0.672	Remote Similarity	NPD7100	Approved
0.6698	Remote Similarity	NPD4788	Approved
0.6696	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6641	Remote Similarity	NPD6067	Discontinued
0.664	Remote Similarity	NPD6335	Approved
0.6638	Remote Similarity	NPD5223	Approved
0.6636	Remote Similarity	NPD4786	Approved
0.6615	Remote Similarity	NPD8074	Phase 3
0.6613	Remote Similarity	NPD6868	Approved
0.6612	Remote Similarity	NPD6371	Approved
0.661	Remote Similarity	NPD5141	Approved
0.6609	Remote Similarity	NPD5696	Approved
0.6607	Remote Similarity	NPD8171	Discontinued
0.6607	Remote Similarity	NPD4202	Approved
0.6606	Remote Similarity	NPD3573	Approved
0.6583	Remote Similarity	NPD4729	Approved
0.6583	Remote Similarity	NPD4730	Approved
0.6581	Remote Similarity	NPD7632	Discontinued
0.656	Remote Similarity	NPD6317	Approved
0.6557	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD4767	Approved
0.6555	Remote Similarity	NPD4768	Approved
0.6545	Remote Similarity	NPD5737	Approved
0.6545	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6672	Approved
0.6514	Remote Similarity	NPD7146	Approved
0.6514	Remote Similarity	NPD6684	Approved
0.6514	Remote Similarity	NPD7521	Approved
0.6514	Remote Similarity	NPD6409	Approved
0.6514	Remote Similarity	NPD5330	Approved
0.6514	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7334	Approved
0.6508	Remote Similarity	NPD6313	Approved
0.6508	Remote Similarity	NPD6314	Approved
0.6496	Remote Similarity	NPD1700	Approved
0.6491	Remote Similarity	NPD5695	Phase 3
0.6491	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6101	Approved
0.6486	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6909	Approved
0.6484	Remote Similarity	NPD6908	Approved
0.6484	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6940	Discontinued
0.6475	Remote Similarity	NPD5250	Approved
0.6475	Remote Similarity	NPD5248	Approved
0.6475	Remote Similarity	NPD5251	Approved
0.6475	Remote Similarity	NPD5249	Phase 3
0.6475	Remote Similarity	NPD5247	Approved
0.6471	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5956	Approved
0.6449	Remote Similarity	NPD3667	Approved
0.6446	Remote Similarity	NPD5128	Approved
0.6439	Remote Similarity	NPD8337	Approved
0.6439	Remote Similarity	NPD8336	Approved
0.6429	Remote Similarity	NPD6698	Approved
0.6429	Remote Similarity	NPD46	Approved
0.6408	Remote Similarity	NPD3703	Phase 2
0.6396	Remote Similarity	NPD6903	Approved
0.6389	Remote Similarity	NPD3669	Approved
0.6389	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4754	Approved
0.6372	Remote Similarity	NPD7983	Approved
0.6372	Remote Similarity	NPD7637	Suspended
0.637	Remote Similarity	NPD8338	Approved
0.6355	Remote Similarity	NPD1780	Approved
0.6355	Remote Similarity	NPD1779	Approved
0.6348	Remote Similarity	NPD4629	Approved
0.6348	Remote Similarity	NPD5210	Approved
0.6339	Remote Similarity	NPD4753	Phase 2
0.633	Remote Similarity	NPD3666	Approved
0.633	Remote Similarity	NPD3665	Phase 1
0.633	Remote Similarity	NPD3133	Approved
0.6316	Remote Similarity	NPD5778	Approved
0.6316	Remote Similarity	NPD5779	Approved
0.6296	Remote Similarity	NPD7260	Phase 2
0.629	Remote Similarity	NPD5216	Approved
0.629	Remote Similarity	NPD5217	Approved
0.629	Remote Similarity	NPD5215	Approved
0.6275	Remote Similarity	NPD4808	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