NPASS Compound

Structure

NPC170615 OpenBabel07101718222D 28 31 0 0 1 0 0 0 0 0999 V2000 -1.4057 2.0619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1797 3.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2864 0.2065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7686 1.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2338 1.5239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2200 0.9729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2028 2.0833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8868 -0.3790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6014 -0.3472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0267 1.1751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4534 2.5412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5213 0.3472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5429 1.1274 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2028 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8042 1.7361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6014 1.7361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2028 0.6944 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.6944 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0864 0.9605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8042 1.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6014 1.0417 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4592 2.8529 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3283 2.0676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0380 -0.4822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6394 2.2183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0690 2.7005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6398 1.5950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 11 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 23 2 0 0 0 0 11 28 1 0 0 0 0 12 6 1 1 0 0 0 13 18 1 0 0 0 0 13 24 1 6 0 0 0 14 17 1 0 0 0 0 14 25 2 0 0 0 0 15 20 1 0 0 0 0 15 26 1 6 0 0 0 16 21 1 1 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 1 0 0 0 18 21 1 1 0 0 0 18 22 1 0 0 0 0 19 22 1 1 0 0 0 19 28 1 0 0 0 0 21 5 1 1 0 0 0 22 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.22
Volume:	399.674
LogP:	1.777
LogD:	2.064
LogS:	-3.327
# Rotatable Bonds:	2
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.463
Synthetic Accessibility Score:	6.325
Fsp3:	0.818
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:	-5.505
MDCK Permeability:	9.629959095036611e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.79
30% Bioavailability (F30%):	0.792

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	41.128990173339844%
Volume Distribution (VD):	0.558
Pgp-substrate:	62.520790100097656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.148
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.547
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.229
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	5.331
Half-life (T1/2):	0.559

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.306
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.123
Rat Oral Acute Toxicity:	0.618
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.181
Carcinogencity:	0.286
Eye Corrosion:	0.026
Eye Irritation:	0.019
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC170615

Natural Product ID:	NPC170615
*Common Name:**	Nervonin J
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZCRPVWMRYCOZCH-BGNALAMCSA-N
Standard InCHI:	InChI=1S/C22H32O6/c1-10-12-6-13(24)18-21(5)16(27)7-15(26)20(3,4)17(21)14(25)9-22(18,8-12)19(10)28-11(2)23/h12-13,15-19,24,26-27H,1,6-9H2,2-5H3/t12-,13+,15+,16+,17-,18+,19-,21-,22+/m1/s1
SMILES:	CC(=O)O[C@@H]1C(=C)[C@H]2C[C@]31CC(=O)[C@H]1[C@@]([C@@H]3[C@H](C2)O)(C)[C@@H](O)C[C@@H](C1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513483
PubChem CID:	24861907
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
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18345641]
NPO8269	Isodon nervosus	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
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[569840]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[569840]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[569840]

☑ 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 NPC170615 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	225
0.1-0.2	1646
0.2-0.3	5225
0.3-0.4	9457
0.4-0.5	11482
0.5-0.6	5609
0.6-0.7	5981
0.7-0.8	2683
0.8-0.85	258
0.85-0.9	94
0.9-0.95	30
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9691	High Similarity	NPC28791
0.9691	High Similarity	NPC295366
0.9684	High Similarity	NPC121218
0.9684	High Similarity	NPC253886
0.9592	High Similarity	NPC86852
0.9592	High Similarity	NPC251824
0.9388	High Similarity	NPC47281
0.9293	High Similarity	NPC37600
0.9293	High Similarity	NPC50535
0.9278	High Similarity	NPC295276
0.9271	High Similarity	NPC162459
0.9271	High Similarity	NPC28864
0.9271	High Similarity	NPC20479
0.9271	High Similarity	NPC38471
0.9271	High Similarity	NPC98837
0.9271	High Similarity	NPC38296
0.9216	High Similarity	NPC94650
0.9175	High Similarity	NPC293866
0.9082	High Similarity	NPC46848
0.9072	High Similarity	NPC89099
0.9062	High Similarity	NPC200054
0.9062	High Similarity	NPC29410
0.9043	High Similarity	NPC130840
0.899	High Similarity	NPC214946
0.899	High Similarity	NPC286519
0.899	High Similarity	NPC76866
0.899	High Similarity	NPC148628
0.899	High Similarity	NPC246736
0.899	High Similarity	NPC88203
0.899	High Similarity	NPC275990
0.899	High Similarity	NPC304832
0.8969	High Similarity	NPC10864
0.8958	High Similarity	NPC98639
0.89	High Similarity	NPC87927
0.89	High Similarity	NPC469985
0.8889	High Similarity	NPC52899
0.8889	High Similarity	NPC289148
0.8889	High Similarity	NPC163963
0.8878	High Similarity	NPC471038
0.8854	High Similarity	NPC3359
0.8812	High Similarity	NPC301787
0.8788	High Similarity	NPC287676
0.8762	High Similarity	NPC40608
0.875	High Similarity	NPC294263
0.875	High Similarity	NPC124053
0.875	High Similarity	NPC199543
0.8738	High Similarity	NPC218123
0.8738	High Similarity	NPC112895
0.8738	High Similarity	NPC231278
0.8737	High Similarity	NPC194485
0.8737	High Similarity	NPC219937
0.8737	High Similarity	NPC53890
0.8737	High Similarity	NPC123252
0.8737	High Similarity	NPC100313
0.8725	High Similarity	NPC200957
0.8725	High Similarity	NPC138908
0.8725	High Similarity	NPC222833
0.87	High Similarity	NPC39683
0.87	High Similarity	NPC252614
0.8687	High Similarity	NPC16911
0.8687	High Similarity	NPC78427
0.8687	High Similarity	NPC474793
0.8673	High Similarity	NPC329910
0.8667	High Similarity	NPC471251
0.866	High Similarity	NPC280804
0.8654	High Similarity	NPC471250
0.8641	High Similarity	NPC176949
0.8641	High Similarity	NPC201908
0.8641	High Similarity	NPC166993
0.8627	High Similarity	NPC84928
0.8627	High Similarity	NPC98603
0.8627	High Similarity	NPC29705
0.86	High Similarity	NPC108371
0.86	High Similarity	NPC180733
0.86	High Similarity	NPC37047
0.86	High Similarity	NPC94906
0.86	High Similarity	NPC41971
0.8586	High Similarity	NPC274793
0.8585	High Similarity	NPC476964
0.8571	High Similarity	NPC259042
0.8571	High Similarity	NPC470232
0.8571	High Similarity	NPC470229
0.8571	High Similarity	NPC157686
0.8558	High Similarity	NPC273155
0.8557	High Similarity	NPC26046
0.8557	High Similarity	NPC244356
0.8557	High Similarity	NPC224060
0.8544	High Similarity	NPC231530
0.8544	High Similarity	NPC278628
0.8529	High Similarity	NPC122811
0.8529	High Similarity	NPC209298
0.8529	High Similarity	NPC139347
0.8529	High Similarity	NPC221421
0.8529	High Similarity	NPC216114
0.8529	High Similarity	NPC277074
0.8529	High Similarity	NPC140723
0.8526	High Similarity	NPC160304
0.8515	High Similarity	NPC471790
0.8515	High Similarity	NPC75941
0.8515	High Similarity	NPC236585
0.8511	High Similarity	NPC472505
0.85	High Similarity	NPC472028
0.85	High Similarity	NPC476806
0.85	High Similarity	NPC469986
0.85	High Similarity	NPC476807
0.8485	Intermediate Similarity	NPC234564
0.8485	Intermediate Similarity	NPC13949
0.8469	Intermediate Similarity	NPC469596
0.8469	Intermediate Similarity	NPC148000
0.8469	Intermediate Similarity	NPC470385
0.8469	Intermediate Similarity	NPC470386
0.8469	Intermediate Similarity	NPC225474
0.8469	Intermediate Similarity	NPC475118
0.8469	Intermediate Similarity	NPC47853
0.8462	Intermediate Similarity	NPC471246
0.8454	Intermediate Similarity	NPC198054
0.8431	Intermediate Similarity	NPC124544
0.8421	Intermediate Similarity	NPC472497
0.8421	Intermediate Similarity	NPC472495
0.8416	Intermediate Similarity	NPC218383
0.8416	Intermediate Similarity	NPC293890
0.8416	Intermediate Similarity	NPC470388
0.84	Intermediate Similarity	NPC111187
0.84	Intermediate Similarity	NPC473963
0.84	Intermediate Similarity	NPC190080
0.84	Intermediate Similarity	NPC253586
0.8396	Intermediate Similarity	NPC255655
0.8384	Intermediate Similarity	NPC205173
0.8384	Intermediate Similarity	NPC241047
0.8384	Intermediate Similarity	NPC210214
0.8384	Intermediate Similarity	NPC263135
0.8384	Intermediate Similarity	NPC288906
0.8381	Intermediate Similarity	NPC94529
0.8381	Intermediate Similarity	NPC211224
0.8367	Intermediate Similarity	NPC476189
0.8367	Intermediate Similarity	NPC472496
0.8365	Intermediate Similarity	NPC285927
0.8365	Intermediate Similarity	NPC4115
0.835	Intermediate Similarity	NPC266
0.835	Intermediate Similarity	NPC470310
0.835	Intermediate Similarity	NPC96217
0.8349	Intermediate Similarity	NPC469794
0.8349	Intermediate Similarity	NPC72772
0.8333	Intermediate Similarity	NPC475958
0.8333	Intermediate Similarity	NPC148279
0.8333	Intermediate Similarity	NPC49532
0.8333	Intermediate Similarity	NPC474327
0.8318	Intermediate Similarity	NPC470281
0.8318	Intermediate Similarity	NPC329953
0.8318	Intermediate Similarity	NPC470311
0.8318	Intermediate Similarity	NPC270586
0.8317	Intermediate Similarity	NPC119036
0.83	Intermediate Similarity	NPC256227
0.83	Intermediate Similarity	NPC306797
0.83	Intermediate Similarity	NPC169270
0.83	Intermediate Similarity	NPC93245
0.83	Intermediate Similarity	NPC292718
0.83	Intermediate Similarity	NPC111834
0.83	Intermediate Similarity	NPC470387
0.83	Intermediate Similarity	NPC219353
0.83	Intermediate Similarity	NPC473964
0.8298	Intermediate Similarity	NPC299963
0.8283	Intermediate Similarity	NPC29247
0.8283	Intermediate Similarity	NPC104371
0.8283	Intermediate Similarity	NPC111524
0.8283	Intermediate Similarity	NPC289539
0.8283	Intermediate Similarity	NPC215271
0.8283	Intermediate Similarity	NPC153775
0.8283	Intermediate Similarity	NPC303863
0.8283	Intermediate Similarity	NPC24861
0.8283	Intermediate Similarity	NPC469982
0.8283	Intermediate Similarity	NPC91772
0.8283	Intermediate Similarity	NPC292374
0.8283	Intermediate Similarity	NPC129004
0.8283	Intermediate Similarity	NPC261333
0.8283	Intermediate Similarity	NPC101233
0.8269	Intermediate Similarity	NPC310586
0.8269	Intermediate Similarity	NPC13149
0.8269	Intermediate Similarity	NPC96268
0.8269	Intermediate Similarity	NPC474558
0.8269	Intermediate Similarity	NPC202793
0.8265	Intermediate Similarity	NPC470230
0.8265	Intermediate Similarity	NPC198242
0.8265	Intermediate Similarity	NPC250753
0.8265	Intermediate Similarity	NPC211403
0.8252	Intermediate Similarity	NPC15396
0.8252	Intermediate Similarity	NPC22388
0.8252	Intermediate Similarity	NPC193934
0.8252	Intermediate Similarity	NPC309388
0.8252	Intermediate Similarity	NPC271980
0.8252	Intermediate Similarity	NPC475803
0.8247	Intermediate Similarity	NPC194642
0.8235	Intermediate Similarity	NPC47024
0.8235	Intermediate Similarity	NPC267921
0.8229	Intermediate Similarity	NPC153604
0.8224	Intermediate Similarity	NPC471093
0.8224	Intermediate Similarity	NPC130302
0.8224	Intermediate Similarity	NPC98633
0.8208	Intermediate Similarity	NPC63841
0.8208	Intermediate Similarity	NPC189075

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 NPC170615 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	2009
0.2-0.3	3930
0.3-0.4	1955
0.4-0.5	544
0.5-0.6	231
0.6-0.7	160
0.7-0.8	103
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8137	Intermediate Similarity	NPD7638	Approved
0.8081	Intermediate Similarity	NPD8035	Phase 2
0.8081	Intermediate Similarity	NPD8034	Phase 2
0.8058	Intermediate Similarity	NPD7639	Approved
0.8058	Intermediate Similarity	NPD7640	Approved
0.8037	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD5739	Approved
0.8019	Intermediate Similarity	NPD7128	Approved
0.8019	Intermediate Similarity	NPD6675	Approved
0.8019	Intermediate Similarity	NPD6402	Approved
0.7963	Intermediate Similarity	NPD6373	Approved
0.7963	Intermediate Similarity	NPD6372	Approved
0.787	Intermediate Similarity	NPD6881	Approved
0.787	Intermediate Similarity	NPD6899	Approved
0.787	Intermediate Similarity	NPD7320	Approved
0.7838	Intermediate Similarity	NPD8133	Approved
0.7835	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6649	Approved
0.7818	Intermediate Similarity	NPD6650	Approved
0.7778	Intermediate Similarity	NPD5697	Approved
0.7778	Intermediate Similarity	NPD5701	Approved
0.7727	Intermediate Similarity	NPD7290	Approved
0.7727	Intermediate Similarity	NPD6883	Approved
0.7727	Intermediate Similarity	NPD7102	Approved
0.7712	Intermediate Similarity	NPD7507	Approved
0.7685	Intermediate Similarity	NPD6008	Approved
0.7667	Intermediate Similarity	NPD7319	Approved
0.7658	Intermediate Similarity	NPD6869	Approved
0.7658	Intermediate Similarity	NPD6847	Approved
0.7658	Intermediate Similarity	NPD8130	Phase 1
0.7658	Intermediate Similarity	NPD6617	Approved
0.7647	Intermediate Similarity	NPD6399	Phase 3
0.7636	Intermediate Similarity	NPD6012	Approved
0.7636	Intermediate Similarity	NPD6014	Approved
0.7636	Intermediate Similarity	NPD6013	Approved
0.7589	Intermediate Similarity	NPD8297	Approved
0.7589	Intermediate Similarity	NPD6882	Approved
0.757	Intermediate Similarity	NPD7632	Discontinued
0.7545	Intermediate Similarity	NPD6011	Approved
0.7524	Intermediate Similarity	NPD4755	Approved
0.7522	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6697	Approved
0.7474	Intermediate Similarity	NPD6115	Approved
0.7474	Intermediate Similarity	NPD6118	Approved
0.7474	Intermediate Similarity	NPD6114	Approved
0.7436	Intermediate Similarity	NPD6319	Approved
0.7407	Intermediate Similarity	NPD5211	Phase 2
0.7383	Intermediate Similarity	NPD5286	Approved
0.7383	Intermediate Similarity	NPD4700	Approved
0.7383	Intermediate Similarity	NPD5285	Approved
0.7383	Intermediate Similarity	NPD4696	Approved
0.7368	Intermediate Similarity	NPD6116	Phase 1
0.7358	Intermediate Similarity	NPD6083	Phase 2
0.7358	Intermediate Similarity	NPD6084	Phase 2
0.7358	Intermediate Similarity	NPD7902	Approved
0.7353	Intermediate Similarity	NPD5328	Approved
0.7333	Intermediate Similarity	NPD7492	Approved
0.7328	Intermediate Similarity	NPD6009	Approved
0.7321	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7736	Approved
0.7288	Intermediate Similarity	NPD6059	Approved
0.7288	Intermediate Similarity	NPD6054	Approved
0.7281	Intermediate Similarity	NPD6053	Discontinued
0.7273	Intermediate Similarity	NPD4788	Approved
0.7273	Intermediate Similarity	NPD6616	Approved
0.7273	Intermediate Similarity	NPD5141	Approved
0.7265	Intermediate Similarity	NPD7327	Approved
0.7265	Intermediate Similarity	NPD7328	Approved
0.7263	Intermediate Similarity	NPD6117	Approved
0.7257	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7604	Phase 2
0.7248	Intermediate Similarity	NPD5226	Approved
0.7248	Intermediate Similarity	NPD5224	Approved
0.7248	Intermediate Similarity	NPD5225	Approved
0.7248	Intermediate Similarity	NPD4633	Approved
0.7241	Intermediate Similarity	NPD6274	Approved
0.7238	Intermediate Similarity	NPD7748	Approved
0.7227	Intermediate Similarity	NPD5983	Phase 2
0.7227	Intermediate Similarity	NPD6921	Approved
0.7213	Intermediate Similarity	NPD7078	Approved
0.7213	Intermediate Similarity	NPD8293	Discontinued
0.7212	Intermediate Similarity	NPD7515	Phase 2
0.7212	Intermediate Similarity	NPD6079	Approved
0.7203	Intermediate Similarity	NPD7101	Approved
0.7203	Intermediate Similarity	NPD7100	Approved
0.7203	Intermediate Similarity	NPD7516	Approved
0.7182	Intermediate Similarity	NPD5174	Approved
0.7182	Intermediate Similarity	NPD5175	Approved
0.7179	Intermediate Similarity	NPD7115	Discovery
0.7167	Intermediate Similarity	NPD6370	Approved
0.7158	Intermediate Similarity	NPD3703	Phase 2
0.7156	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD4202	Approved
0.7131	Intermediate Similarity	NPD6336	Discontinued
0.713	Intermediate Similarity	NPD5696	Approved
0.7119	Intermediate Similarity	NPD6335	Approved
0.7105	Intermediate Similarity	NPD4634	Approved
0.7103	Intermediate Similarity	NPD4697	Phase 3
0.7087	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8378	Approved
0.7083	Intermediate Similarity	NPD8335	Approved
0.7083	Intermediate Similarity	NPD6909	Approved
0.7083	Intermediate Similarity	NPD6016	Approved
0.7083	Intermediate Similarity	NPD8296	Approved
0.7083	Intermediate Similarity	NPD6908	Approved
0.7083	Intermediate Similarity	NPD8380	Approved
0.7083	Intermediate Similarity	NPD6015	Approved
0.7083	Intermediate Similarity	NPD8379	Approved
0.708	Intermediate Similarity	NPD6686	Approved
0.7075	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7900	Approved
0.7059	Intermediate Similarity	NPD7521	Approved
0.7059	Intermediate Similarity	NPD7334	Approved
0.7059	Intermediate Similarity	NPD3618	Phase 1
0.7059	Intermediate Similarity	NPD6684	Approved
0.7059	Intermediate Similarity	NPD5330	Approved
0.7059	Intermediate Similarity	NPD6409	Approved
0.7059	Intermediate Similarity	NPD7146	Approved
0.7054	Intermediate Similarity	NPD4767	Approved
0.7054	Intermediate Similarity	NPD4768	Approved
0.7053	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6317	Approved
0.703	Intermediate Similarity	NPD4786	Approved
0.7027	Intermediate Similarity	NPD4754	Approved
0.7025	Intermediate Similarity	NPD5988	Approved
0.7018	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5695	Phase 3
0.7	Intermediate Similarity	NPD8377	Approved
0.7	Intermediate Similarity	NPD8294	Approved
0.6991	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6314	Approved
0.6975	Remote Similarity	NPD6313	Approved
0.6967	Remote Similarity	NPD8328	Phase 3
0.6964	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5222	Approved
0.6944	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5221	Approved
0.6942	Remote Similarity	NPD8033	Approved
0.6942	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4729	Approved
0.693	Remote Similarity	NPD5128	Approved
0.693	Remote Similarity	NPD4730	Approved
0.6923	Remote Similarity	NPD6903	Approved
0.6891	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5693	Phase 1
0.6881	Remote Similarity	NPD5173	Approved
0.6863	Remote Similarity	NPD3665	Phase 1
0.6863	Remote Similarity	NPD3133	Approved
0.6863	Remote Similarity	NPD3666	Approved
0.6857	Remote Similarity	NPD4753	Phase 2
0.6842	Remote Similarity	NPD5777	Approved
0.6842	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6435	Approved
0.6832	Remote Similarity	NPD3667	Approved
0.6818	Remote Similarity	NPD4225	Approved
0.681	Remote Similarity	NPD5250	Approved
0.681	Remote Similarity	NPD5251	Approved
0.681	Remote Similarity	NPD5248	Approved
0.681	Remote Similarity	NPD5249	Phase 3
0.681	Remote Similarity	NPD5247	Approved
0.6807	Remote Similarity	NPD6868	Approved
0.6804	Remote Similarity	NPD3702	Approved
0.68	Remote Similarity	NPD7525	Registered
0.6762	Remote Similarity	NPD6672	Approved
0.6762	Remote Similarity	NPD5737	Approved
0.6752	Remote Similarity	NPD5217	Approved
0.6752	Remote Similarity	NPD5216	Approved
0.6752	Remote Similarity	NPD5215	Approved
0.6746	Remote Similarity	NPD6033	Approved
0.6737	Remote Similarity	NPD4244	Approved
0.6737	Remote Similarity	NPD4245	Approved
0.6731	Remote Similarity	NPD6098	Approved
0.6729	Remote Similarity	NPD7637	Suspended
0.6729	Remote Similarity	NPD5284	Approved
0.6729	Remote Similarity	NPD5281	Approved
0.6729	Remote Similarity	NPD6411	Approved
0.6698	Remote Similarity	NPD6080	Approved
0.6698	Remote Similarity	NPD6051	Approved
0.6698	Remote Similarity	NPD6673	Approved
0.6698	Remote Similarity	NPD6904	Approved
0.6697	Remote Similarity	NPD5210	Approved
0.6697	Remote Similarity	NPD4629	Approved
0.6696	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6634	Remote Similarity	NPD5368	Approved
0.6632	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3698	Phase 2
0.661	Remote Similarity	NPD5127	Approved
0.6606	Remote Similarity	NPD6001	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