NPASS Compound

Structure

CID264477 OpenBabel06191716062D 33 36 0 0 1 0 0 0 0 0999 V2000 2.4513 -0.2208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2863 1.8076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0165 -3.0763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7721 -1.5416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4990 -0.6674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4561 -5.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7922 -1.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0882 -2.4759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9892 -0.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3168 0.1646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3853 0.8655 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7205 -2.4424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1460 -2.5749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1372 -0.3091 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3256 -2.1013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9402 -1.2358 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8412 0.3248 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7834 0.4238 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5137 1.0912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9490 -3.5016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8844 0.1981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6039 -0.0499 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9422 0.0990 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5236 -1.5158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8798 1.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0480 -3.7944 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2697 1.0635 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6531 -4.1355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6215 -2.7352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4559 1.1903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9981 -1.3348 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 6.6039 0.8975 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 12 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 13 2 0 0 0 0 9 22 1 0 0 0 0 10 19 1 0 0 0 0 11 23 1 1 0 0 0 11 32 1 0 0 0 0 12 24 2 0 0 0 0 12 29 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 10 1 1 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 29 1 6 0 0 0 16 31 1 1 0 0 0 17 18 1 0 0 0 0 17 30 1 6 0 0 0 18 22 1 1 0 0 0 18 33 1 0 0 0 0 19 25 2 0 0 0 0 19 30 1 0 0 0 0 20 26 2 0 0 0 0 20 28 1 0 0 0 0 21 23 1 0 0 0 0 21 27 2 0 0 0 0 21 31 1 0 0 0 0 22 4 1 1 0 0 0 22 33 1 0 0 0 0 23 5 1 6 0 0 0 23 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.17
Volume:	444.222
LogP:	1.802
LogD:	1.307
LogS:	-3.945
# Rotatable Bonds:	7
TPSA:	130.26
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	5.453
Fsp3:	0.652
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:	-5.033
MDCK Permeability:	0.00010390407260274515
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.154
20% Bioavailability (F20%):	0.961
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.269
Plasma Protein Binding (PPB):	33.85155487060547%
Volume Distribution (VD):	1.346
Pgp-substrate:	36.890716552734375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.368
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.366
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.102
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.699
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	7.802
Half-life (T1/2):	0.244

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.799
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.762
Rat Oral Acute Toxicity:	0.378
Maximum Recommended Daily Dose:	0.562
Skin Sensitization:	0.768
Carcinogencity:	0.263
Eye Corrosion:	0.188
Eye Irritation:	0.052
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC264477

Natural Product ID:	NPC264477
*Common Name:**	Enhydrin
IUPAC Name:	n.a.
Synonyms:	Enhydrin; Enhydrine
Standard InCHIKey:	VCBNPTWPJQLHQN-ZRVFLOPNSA-N
Standard InCHI:	InChI=1S/C23H28O10/c1-10-14-16(31-21(27)23(5)11(2)32-23)15(29-12(3)24)13(20(26)28-6)8-7-9-22(4)18(33-22)17(14)30-19(10)25/h8,11,14-18H,1,7,9H2,2-6H3/b13-8+/t11-,14+,15-,16-,17-,18+,22+,23-/m0/s1
SMILES:	COC(=O)/C/1=C/CC[C@@]2(C)O[C@@H]2[C@@H]2[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)[C@@]1(C)O[C@H]1C)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL206765
PubChem CID:	44409570
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO24243	Smallanthus sonchifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28268	Enhydra fluctuans	Species	Mustelidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28268	Enhydra fluctuans	Species	Mustelidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24243	Smallanthus sonchifolius	Species	Asteraceae	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	5
Others	1

Activity Type	# Activity
CELL-LINE	1
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	600.0	nM	PMID[532208]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	10.0	uM	PMID[532206]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	8760.0	nM	PMID[532207]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	2951.21	nM	PMID[532209]
NPT27	Others	Unspecified		IC50	=	7490.0	nM	PMID[532209]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	2950.0	nM	PMID[532209]

☑ 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 NPC264477 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	290
0.1-0.2	1852
0.2-0.3	6240
0.3-0.4	11364
0.4-0.5	13777
0.5-0.6	5998
0.6-0.7	2496
0.7-0.8	513
0.8-0.85	108
0.85-0.9	42
0.9-0.95	6
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477511
0.9688	High Similarity	NPC471143
0.9688	High Similarity	NPC477510
0.9681	High Similarity	NPC477512
0.9677	High Similarity	NPC471140
0.957	High Similarity	NPC17585
0.949	High Similarity	NPC477513
0.9355	High Similarity	NPC471147
0.9167	High Similarity	NPC208233
0.9158	High Similarity	NPC35498
0.9082	High Similarity	NPC471148
0.898	High Similarity	NPC164598
0.898	High Similarity	NPC474339
0.8947	High Similarity	NPC473330
0.8947	High Similarity	NPC140543
0.8947	High Similarity	NPC473316
0.8936	High Similarity	NPC20713
0.8925	High Similarity	NPC166919
0.8925	High Similarity	NPC151770
0.8889	High Similarity	NPC149371
0.8878	High Similarity	NPC475949
0.8878	High Similarity	NPC288876
0.8854	High Similarity	NPC475659
0.883	High Similarity	NPC475748
0.8788	High Similarity	NPC47880
0.8788	High Similarity	NPC201718
0.8776	High Similarity	NPC471144
0.8763	High Similarity	NPC473859
0.875	High Similarity	NPC476267
0.871	High Similarity	NPC231889
0.871	High Similarity	NPC266957
0.8646	High Similarity	NPC165383
0.8602	High Similarity	NPC50637
0.8571	High Similarity	NPC230800
0.8571	High Similarity	NPC279621
0.8571	High Similarity	NPC476275
0.8529	High Similarity	NPC474741
0.8495	Intermediate Similarity	NPC38468
0.8495	Intermediate Similarity	NPC50362
0.8495	Intermediate Similarity	NPC319795
0.8469	Intermediate Similarity	NPC471142
0.8438	Intermediate Similarity	NPC49342
0.8438	Intermediate Similarity	NPC329857
0.8438	Intermediate Similarity	NPC469718
0.8438	Intermediate Similarity	NPC312042
0.8438	Intermediate Similarity	NPC251385
0.8431	Intermediate Similarity	NPC19239
0.8431	Intermediate Similarity	NPC474166
0.8421	Intermediate Similarity	NPC475902
0.8416	Intermediate Similarity	NPC476270
0.84	Intermediate Similarity	NPC474213
0.84	Intermediate Similarity	NPC279561
0.84	Intermediate Similarity	NPC473326
0.8396	Intermediate Similarity	NPC475495
0.8384	Intermediate Similarity	NPC476315
0.8367	Intermediate Similarity	NPC474247
0.8367	Intermediate Similarity	NPC303942
0.8367	Intermediate Similarity	NPC57405
0.8365	Intermediate Similarity	NPC469558
0.8365	Intermediate Similarity	NPC474716
0.8333	Intermediate Similarity	NPC475971
0.8318	Intermediate Similarity	NPC477093
0.8318	Intermediate Similarity	NPC473522
0.8318	Intermediate Similarity	NPC475277
0.8316	Intermediate Similarity	NPC475703
0.8302	Intermediate Similarity	NPC473843
0.8302	Intermediate Similarity	NPC473594
0.8302	Intermediate Similarity	NPC473975
0.8302	Intermediate Similarity	NPC474586
0.8298	Intermediate Similarity	NPC474547
0.8283	Intermediate Similarity	NPC270013
0.8283	Intermediate Similarity	NPC474947
0.8283	Intermediate Similarity	NPC471141
0.8283	Intermediate Similarity	NPC14961
0.828	Intermediate Similarity	NPC272814
0.8269	Intermediate Similarity	NPC9303
0.8269	Intermediate Similarity	NPC475802
0.8269	Intermediate Similarity	NPC16313
0.8265	Intermediate Similarity	NPC228451
0.8265	Intermediate Similarity	NPC212486
0.8265	Intermediate Similarity	NPC125674
0.8265	Intermediate Similarity	NPC475838
0.8265	Intermediate Similarity	NPC476300
0.8252	Intermediate Similarity	NPC475871
0.8252	Intermediate Similarity	NPC472755
0.8252	Intermediate Similarity	NPC475945
0.8235	Intermediate Similarity	NPC15993
0.8235	Intermediate Similarity	NPC474742
0.8224	Intermediate Similarity	NPC194619
0.8211	Intermediate Similarity	NPC204048
0.8191	Intermediate Similarity	NPC470238
0.8191	Intermediate Similarity	NPC138647
0.819	Intermediate Similarity	NPC475587
0.819	Intermediate Similarity	NPC194620
0.819	Intermediate Similarity	NPC326994
0.819	Intermediate Similarity	NPC324327
0.819	Intermediate Similarity	NPC475510
0.819	Intermediate Similarity	NPC474421
0.819	Intermediate Similarity	NPC72813
0.8182	Intermediate Similarity	NPC474035
0.8182	Intermediate Similarity	NPC81386
0.8155	Intermediate Similarity	NPC324017
0.8155	Intermediate Similarity	NPC472754
0.8155	Intermediate Similarity	NPC320019
0.8155	Intermediate Similarity	NPC474747
0.8137	Intermediate Similarity	NPC469551
0.8125	Intermediate Similarity	NPC5130
0.8113	Intermediate Similarity	NPC14862
0.8113	Intermediate Similarity	NPC169888
0.8113	Intermediate Similarity	NPC474664
0.8113	Intermediate Similarity	NPC233379
0.8113	Intermediate Similarity	NPC327286
0.8113	Intermediate Similarity	NPC473939
0.8113	Intermediate Similarity	NPC473595
0.8113	Intermediate Similarity	NPC55972
0.81	Intermediate Similarity	NPC477922
0.81	Intermediate Similarity	NPC36954
0.8081	Intermediate Similarity	NPC475912
0.8065	Intermediate Similarity	NPC141810
0.8061	Intermediate Similarity	NPC51004
0.8061	Intermediate Similarity	NPC62815
0.8061	Intermediate Similarity	NPC473619
0.8058	Intermediate Similarity	NPC46998
0.8058	Intermediate Similarity	NPC128733
0.8058	Intermediate Similarity	NPC185141
0.8058	Intermediate Similarity	NPC110443
0.8058	Intermediate Similarity	NPC472753
0.8058	Intermediate Similarity	NPC133907
0.8041	Intermediate Similarity	NPC469628
0.8041	Intermediate Similarity	NPC469631
0.8041	Intermediate Similarity	NPC471047
0.8041	Intermediate Similarity	NPC469653
0.8041	Intermediate Similarity	NPC475906
0.8037	Intermediate Similarity	NPC38154
0.8037	Intermediate Similarity	NPC475922
0.8037	Intermediate Similarity	NPC15218
0.802	Intermediate Similarity	NPC76862
0.802	Intermediate Similarity	NPC39859
0.802	Intermediate Similarity	NPC470883
0.802	Intermediate Similarity	NPC477921
0.802	Intermediate Similarity	NPC158416
0.8018	Intermediate Similarity	NPC471146
0.8018	Intermediate Similarity	NPC475305
0.8	Intermediate Similarity	NPC472756
0.8	Intermediate Similarity	NPC190294
0.798	Intermediate Similarity	NPC70251
0.798	Intermediate Similarity	NPC473321
0.798	Intermediate Similarity	NPC475881
0.798	Intermediate Similarity	NPC30515
0.798	Intermediate Similarity	NPC184463
0.7963	Intermediate Similarity	NPC281624
0.7963	Intermediate Similarity	NPC115257
0.7963	Intermediate Similarity	NPC161816
0.7959	Intermediate Similarity	NPC474032
0.7959	Intermediate Similarity	NPC307411
0.7946	Intermediate Similarity	NPC475401
0.7938	Intermediate Similarity	NPC471739
0.7928	Intermediate Similarity	NPC474333
0.7925	Intermediate Similarity	NPC223450
0.7905	Intermediate Similarity	NPC4620
0.7905	Intermediate Similarity	NPC475873
0.79	Intermediate Similarity	NPC288240
0.79	Intermediate Similarity	NPC81419
0.79	Intermediate Similarity	NPC273579
0.79	Intermediate Similarity	NPC475302
0.79	Intermediate Similarity	NPC179746
0.79	Intermediate Similarity	NPC295204
0.79	Intermediate Similarity	NPC162205
0.7895	Intermediate Similarity	NPC474703
0.7895	Intermediate Similarity	NPC128429
0.7879	Intermediate Similarity	NPC144133
0.7879	Intermediate Similarity	NPC475855
0.7879	Intermediate Similarity	NPC179394
0.7876	Intermediate Similarity	NPC477092
0.7872	Intermediate Similarity	NPC207188
0.787	Intermediate Similarity	NPC471934
0.7857	Intermediate Similarity	NPC202672
0.7857	Intermediate Similarity	NPC296822
0.7857	Intermediate Similarity	NPC287089
0.785	Intermediate Similarity	NPC26617
0.7849	Intermediate Similarity	NPC617
0.7843	Intermediate Similarity	NPC299396
0.7843	Intermediate Similarity	NPC31645
0.7843	Intermediate Similarity	NPC476009
0.7843	Intermediate Similarity	NPC301596
0.7843	Intermediate Similarity	NPC172998
0.7835	Intermediate Similarity	NPC38576
0.7835	Intermediate Similarity	NPC475491
0.7835	Intermediate Similarity	NPC279859
0.7835	Intermediate Similarity	NPC469626
0.7835	Intermediate Similarity	NPC284902
0.783	Intermediate Similarity	NPC100487
0.783	Intermediate Similarity	NPC475676
0.783	Intermediate Similarity	NPC220964
0.7822	Intermediate Similarity	NPC121825
0.7818	Intermediate Similarity	NPC471933
0.7818	Intermediate Similarity	NPC473877
0.781	Intermediate Similarity	NPC105725
0.78	Intermediate Similarity	NPC12172
0.78	Intermediate Similarity	NPC208886

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 NPC264477 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	2474
0.2-0.3	3852
0.3-0.4	1724
0.4-0.5	577
0.5-0.6	225
0.6-0.7	29
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8495	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD46	Approved
0.7525	Intermediate Similarity	NPD6698	Approved
0.7426	Intermediate Similarity	NPD1695	Approved
0.7184	Intermediate Similarity	NPD7838	Discovery
0.7168	Intermediate Similarity	NPD6371	Approved
0.7115	Intermediate Similarity	NPD7983	Approved
0.7075	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5282	Discontinued
0.6818	Remote Similarity	NPD6648	Approved
0.681	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5344	Discontinued
0.6724	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4225	Approved
0.6552	Remote Similarity	NPD6686	Approved
0.6522	Remote Similarity	NPD6008	Approved
0.6515	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6319	Approved
0.6496	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7642	Approved
0.6452	Remote Similarity	NPD8515	Approved
0.6452	Remote Similarity	NPD8516	Approved
0.6452	Remote Similarity	NPD8517	Approved
0.6452	Remote Similarity	NPD8513	Phase 3
0.6452	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5779	Approved
0.6422	Remote Similarity	NPD5778	Approved
0.6408	Remote Similarity	NPD5209	Approved
0.6408	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7115	Discovery
0.6389	Remote Similarity	NPD5785	Approved
0.6381	Remote Similarity	NPD1694	Approved
0.6349	Remote Similarity	NPD7830	Approved
0.6349	Remote Similarity	NPD7829	Approved
0.6333	Remote Similarity	NPD6053	Discontinued
0.6299	Remote Similarity	NPD7492	Approved
0.625	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD7839	Suspended
0.624	Remote Similarity	NPD6054	Approved
0.6226	Remote Similarity	NPD5363	Approved
0.6202	Remote Similarity	NPD8074	Phase 3
0.6202	Remote Similarity	NPD7078	Approved
0.6198	Remote Similarity	NPD8297	Approved
0.619	Remote Similarity	NPD6016	Approved
0.619	Remote Similarity	NPD6015	Approved
0.6168	Remote Similarity	NPD5786	Approved
0.6154	Remote Similarity	NPD7736	Approved
0.6142	Remote Similarity	NPD5988	Approved
0.6142	Remote Similarity	NPD6370	Approved
0.6136	Remote Similarity	NPD7260	Phase 2
0.6134	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6649	Approved
0.6116	Remote Similarity	NPD6650	Approved
0.6111	Remote Similarity	NPD6059	Approved
0.6107	Remote Similarity	NPD7319	Approved
0.6094	Remote Similarity	NPD8328	Phase 3
0.6083	Remote Similarity	NPD6373	Approved
0.6083	Remote Similarity	NPD6372	Approved
0.6077	Remote Similarity	NPD8293	Discontinued
0.605	Remote Similarity	NPD5697	Approved
0.6038	Remote Similarity	NPD7154	Phase 3
0.6036	Remote Similarity	NPD5693	Phase 1
0.6033	Remote Similarity	NPD2067	Discontinued
0.6019	Remote Similarity	NPD4249	Approved
0.6016	Remote Similarity	NPD8080	Discontinued
0.6016	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD8451	Approved
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD8273	Phase 1
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD5369	Approved
0.6	Remote Similarity	NPD6101	Approved
0.5984	Remote Similarity	NPD2204	Approved
0.597	Remote Similarity	NPD6845	Suspended
0.5969	Remote Similarity	NPD7604	Phase 2
0.5966	Remote Similarity	NPD6402	Approved
0.5966	Remote Similarity	NPD7128	Approved
0.5966	Remote Similarity	NPD6675	Approved
0.5966	Remote Similarity	NPD5739	Approved
0.5963	Remote Similarity	NPD4251	Approved
0.5963	Remote Similarity	NPD4250	Approved
0.5954	Remote Similarity	NPD8448	Approved
0.595	Remote Similarity	NPD6012	Approved
0.595	Remote Similarity	NPD6014	Approved
0.595	Remote Similarity	NPD6013	Approved
0.5943	Remote Similarity	NPD4270	Approved
0.5943	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6435	Approved
0.5943	Remote Similarity	NPD4269	Approved
0.5938	Remote Similarity	NPD5983	Phase 2
0.5935	Remote Similarity	NPD6882	Approved
0.5917	Remote Similarity	NPD5701	Approved
0.5909	Remote Similarity	NPD6672	Approved
0.5909	Remote Similarity	NPD5737	Approved
0.5902	Remote Similarity	NPD6883	Approved
0.5902	Remote Similarity	NPD7102	Approved
0.5902	Remote Similarity	NPD7290	Approved
0.5893	Remote Similarity	NPD6411	Approved
0.5888	Remote Similarity	NPD6110	Phase 1
0.5877	Remote Similarity	NPD5695	Phase 3
0.5873	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD7320	Approved
0.5868	Remote Similarity	NPD6011	Approved
0.5862	Remote Similarity	NPD5696	Approved
0.5862	Remote Similarity	NPD7638	Approved
0.5854	Remote Similarity	NPD6869	Approved
0.5854	Remote Similarity	NPD6617	Approved
0.5854	Remote Similarity	NPD8130	Phase 1
0.5854	Remote Similarity	NPD6847	Approved
0.5827	Remote Similarity	NPD7641	Discontinued
0.5821	Remote Similarity	NPD8390	Approved
0.5821	Remote Similarity	NPD8391	Approved
0.5821	Remote Similarity	NPD8392	Approved
0.5814	Remote Similarity	NPD8444	Approved
0.5814	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7640	Approved
0.5812	Remote Similarity	NPD7639	Approved
0.5802	Remote Similarity	NPD8342	Approved
0.5802	Remote Similarity	NPD8340	Approved
0.5802	Remote Similarity	NPD8341	Approved
0.5802	Remote Similarity	NPD8299	Approved
0.578	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6083	Phase 2
0.5776	Remote Similarity	NPD6084	Phase 2
0.5772	Remote Similarity	NPD4634	Approved
0.5769	Remote Similarity	NPD4756	Discovery
0.5758	Remote Similarity	NPD6336	Discontinued
0.5755	Remote Similarity	NPD5368	Approved
0.5755	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD4821	Approved
0.5755	Remote Similarity	NPD4820	Approved
0.5755	Remote Similarity	NPD4819	Approved
0.5755	Remote Similarity	NPD4822	Approved
0.5755	Remote Similarity	NPD4252	Approved
0.5748	Remote Similarity	NPD7500	Approved
0.5741	Remote Similarity	NPD5362	Discontinued
0.5728	Remote Similarity	NPD8039	Approved
0.5725	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6673	Approved
0.5714	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD6080	Approved
0.5692	Remote Similarity	NPD6921	Approved
0.5672	Remote Similarity	NPD6033	Approved
0.5669	Remote Similarity	NPD6274	Approved
0.5664	Remote Similarity	NPD5692	Phase 3
0.5664	Remote Similarity	NPD3168	Discontinued
0.5652	Remote Similarity	NPD8415	Approved
0.563	Remote Similarity	NPD1700	Approved
0.5625	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6050	Approved
0.5614	Remote Similarity	NPD7637	Suspended
0.5614	Remote Similarity	NPD5694	Approved
0.5603	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6401	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