NPASS Compound

Structure

CID288 OpenBabel06191715322D 25 29 0 0 1 0 0 0 0 0999 V2000 -2.0103 -0.5451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8164 2.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6505 2.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7445 -1.2895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9780 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7445 -0.4299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2013 -0.2796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1744 -0.5451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7445 -1.2896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7445 -0.4298 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2335 -0.4298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9780 0.8597 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7445 1.2895 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4890 0.8597 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8597 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.8597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2335 1.2895 0.0000 C 0 0 0 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 1.4890 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2335 -1.2639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7445 2.1236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2777 0.7239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7224 1.2767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8639 0.1030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 5 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 10 1 0 0 0 0 8 25 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 4 1 1 0 0 0 11 19 1 6 0 0 0 11 20 1 0 0 0 0 12 20 1 0 0 0 0 12 21 2 0 0 0 0 13 6 1 6 0 0 0 13 18 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 1 0 0 0 15 18 1 0 0 0 0 15 20 1 6 0 0 0 16 19 1 0 0 0 0 16 23 2 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 19 7 1 6 0 0 0 20 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.16
Volume:	345.099
LogP:	1.475
LogD:	0.75
LogS:	-3.222
# Rotatable Bonds:	0
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	6.864
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.019
MDCK Permeability:	5.760281055700034e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.734
Plasma Protein Binding (PPB):	59.94981384277344%
Volume Distribution (VD):	1.026
Pgp-substrate:	51.77342224121094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.477
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.591
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.228
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	5.157
Half-life (T1/2):	0.217

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.117
Drug-inuced Liver Injury (DILI):	0.247
AMES Toxicity:	0.64
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.835
Carcinogencity:	0.659
Eye Corrosion:	0.908
Eye Irritation:	0.062
Respiratory Toxicity:	0.991

Download Data

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

Natural Product: NPC288

Natural Product ID:	NPC288
*Common Name:**	LWOAEMJVKDXOEG-ZOWAPRDESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LWOAEMJVKDXOEG-ZOWAPRDESA-N
Standard InCHI:	InChI=1S/C20H24O5/c1-9-10-4-5-11-19(7-10,16(9)23)17(24)14(22)15-18(2,3)13-6-12(21)20(11,15)8-25-13/h10-11,13-15,22H,1,4-8H2,2-3H3/t10-,11-,13+,14+,15-,19+,20-/m1/s1
SMILES:	C=C1[C@@H]2CC[C@@H]3[C@](C1=O)(C2)C(=O)[C@@H](O)[C@H]1[C@@]23CO[C@H](C1(C)C)CC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL426206
PubChem CID:	11782888
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
NPO1927.1	Isodon eriocalyx var. laxiflora	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502334]
NPO1927.1	Isodon eriocalyx var. laxiflora	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1927.1	Isodon eriocalyx var. laxiflora	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	3.73	ug.mL-1	PMID[557348]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	27.22	ug.mL-1	PMID[557348]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	33.16	ug.mL-1	PMID[557348]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	8.87	ug.mL-1	PMID[557348]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16.94	ug.mL-1	PMID[557348]

☑ 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 NPC288 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	251
0.1-0.2	2025
0.2-0.3	7480
0.3-0.4	13249
0.4-0.5	8301
0.5-0.6	5787
0.6-0.7	4241
0.7-0.8	1199
0.8-0.85	147
0.85-0.9	13
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC109059
0.9355	High Similarity	NPC165616
0.898	High Similarity	NPC266
0.8878	High Similarity	NPC272472
0.8776	High Similarity	NPC60947
0.8723	High Similarity	NPC250753
0.8687	High Similarity	NPC163249
0.8673	High Similarity	NPC156324
0.8673	High Similarity	NPC55503
0.8632	High Similarity	NPC82138
0.8632	High Similarity	NPC59170
0.8617	High Similarity	NPC80401
0.8617	High Similarity	NPC180849
0.8602	High Similarity	NPC90676
0.86	High Similarity	NPC139347
0.8586	High Similarity	NPC14634
0.8586	High Similarity	NPC148279
0.8571	High Similarity	NPC146683
0.8571	High Similarity	NPC26270
0.8571	High Similarity	NPC471038
0.8557	High Similarity	NPC13949
0.8557	High Similarity	NPC140242
0.8557	High Similarity	NPC470387
0.8542	High Similarity	NPC302008
0.8542	High Similarity	NPC191094
0.8526	High Similarity	NPC476168
0.8526	High Similarity	NPC278106
0.8515	High Similarity	NPC474558
0.85	High Similarity	NPC475803
0.85	High Similarity	NPC309388
0.8495	Intermediate Similarity	NPC259009
0.8495	Intermediate Similarity	NPC153604
0.8495	Intermediate Similarity	NPC174619
0.8485	Intermediate Similarity	NPC267921
0.8462	Intermediate Similarity	NPC118800
0.8462	Intermediate Similarity	NPC291320
0.8462	Intermediate Similarity	NPC471036
0.8454	Intermediate Similarity	NPC138245
0.8454	Intermediate Similarity	NPC84018
0.8454	Intermediate Similarity	NPC470232
0.8454	Intermediate Similarity	NPC29112
0.8454	Intermediate Similarity	NPC231060
0.8454	Intermediate Similarity	NPC98639
0.8438	Intermediate Similarity	NPC59350
0.8438	Intermediate Similarity	NPC144739
0.8438	Intermediate Similarity	NPC181594
0.8438	Intermediate Similarity	NPC294263
0.8416	Intermediate Similarity	NPC216114
0.8416	Intermediate Similarity	NPC96217
0.8404	Intermediate Similarity	NPC56413
0.84	Intermediate Similarity	NPC46848
0.84	Intermediate Similarity	NPC236585
0.8387	Intermediate Similarity	NPC34190
0.8384	Intermediate Similarity	NPC474793
0.8367	Intermediate Similarity	NPC223169
0.8367	Intermediate Similarity	NPC200054
0.8367	Intermediate Similarity	NPC329910
0.8367	Intermediate Similarity	NPC29410
0.8351	Intermediate Similarity	NPC64006
0.8351	Intermediate Similarity	NPC475118
0.8351	Intermediate Similarity	NPC129004
0.8351	Intermediate Similarity	NPC101233
0.8351	Intermediate Similarity	NPC104371
0.8351	Intermediate Similarity	NPC292374
0.8351	Intermediate Similarity	NPC215271
0.8351	Intermediate Similarity	NPC470386
0.8351	Intermediate Similarity	NPC153775
0.8351	Intermediate Similarity	NPC29247
0.8351	Intermediate Similarity	NPC289539
0.8351	Intermediate Similarity	NPC91772
0.8351	Intermediate Similarity	NPC470385
0.8351	Intermediate Similarity	NPC261333
0.8351	Intermediate Similarity	NPC111524
0.835	Intermediate Similarity	NPC201908
0.835	Intermediate Similarity	NPC176949
0.835	Intermediate Similarity	NPC186054
0.8333	Intermediate Similarity	NPC299185
0.8333	Intermediate Similarity	NPC98603
0.8333	Intermediate Similarity	NPC198242
0.8333	Intermediate Similarity	NPC84928
0.8333	Intermediate Similarity	NPC211403
0.8317	Intermediate Similarity	NPC275990
0.8302	Intermediate Similarity	NPC40608
0.83	Intermediate Similarity	NPC470388
0.8298	Intermediate Similarity	NPC165895
0.8298	Intermediate Similarity	NPC57469
0.8283	Intermediate Similarity	NPC10864
0.828	Intermediate Similarity	NPC102292
0.828	Intermediate Similarity	NPC471034
0.828	Intermediate Similarity	NPC190704
0.8269	Intermediate Similarity	NPC63841
0.8269	Intermediate Similarity	NPC469733
0.8269	Intermediate Similarity	NPC469729
0.8269	Intermediate Similarity	NPC211224
0.8269	Intermediate Similarity	NPC232133
0.8269	Intermediate Similarity	NPC55973
0.8265	Intermediate Similarity	NPC210214
0.8265	Intermediate Similarity	NPC470229
0.8252	Intermediate Similarity	NPC307660
0.8252	Intermediate Similarity	NPC4115
0.8252	Intermediate Similarity	NPC130511
0.8252	Intermediate Similarity	NPC12823
0.8252	Intermediate Similarity	NPC265127
0.8235	Intermediate Similarity	NPC87927
0.8235	Intermediate Similarity	NPC209298
0.8235	Intermediate Similarity	NPC122811
0.8235	Intermediate Similarity	NPC277074
0.8229	Intermediate Similarity	NPC261994
0.8229	Intermediate Similarity	NPC470378
0.8229	Intermediate Similarity	NPC149761
0.8218	Intermediate Similarity	NPC289148
0.8218	Intermediate Similarity	NPC163963
0.8218	Intermediate Similarity	NPC52899
0.82	Intermediate Similarity	NPC28864
0.82	Intermediate Similarity	NPC20479
0.82	Intermediate Similarity	NPC38296
0.82	Intermediate Similarity	NPC98837
0.82	Intermediate Similarity	NPC89099
0.82	Intermediate Similarity	NPC162459
0.82	Intermediate Similarity	NPC38471
0.8191	Intermediate Similarity	NPC120395
0.819	Intermediate Similarity	NPC469983
0.8182	Intermediate Similarity	NPC104568
0.8182	Intermediate Similarity	NPC135548
0.8182	Intermediate Similarity	NPC264979
0.8173	Intermediate Similarity	NPC471474
0.8173	Intermediate Similarity	NPC88833
0.8173	Intermediate Similarity	NPC96333
0.8173	Intermediate Similarity	NPC469746
0.8173	Intermediate Similarity	NPC471461
0.8173	Intermediate Similarity	NPC67745
0.8163	Intermediate Similarity	NPC272635
0.8163	Intermediate Similarity	NPC169751
0.8163	Intermediate Similarity	NPC303863
0.8163	Intermediate Similarity	NPC47853
0.8155	Intermediate Similarity	NPC202793
0.8155	Intermediate Similarity	NPC101842
0.8155	Intermediate Similarity	NPC13149
0.8137	Intermediate Similarity	NPC88203
0.8137	Intermediate Similarity	NPC76866
0.8137	Intermediate Similarity	NPC304832
0.8137	Intermediate Similarity	NPC148628
0.8137	Intermediate Similarity	NPC246736
0.8137	Intermediate Similarity	NPC286519
0.8137	Intermediate Similarity	NPC214946
0.8131	Intermediate Similarity	NPC205534
0.8131	Intermediate Similarity	NPC473352
0.8119	Intermediate Similarity	NPC291785
0.8119	Intermediate Similarity	NPC287676
0.8119	Intermediate Similarity	NPC46761
0.8119	Intermediate Similarity	NPC127408
0.8119	Intermediate Similarity	NPC293866
0.8113	Intermediate Similarity	NPC471093
0.8113	Intermediate Similarity	NPC473324
0.8105	Intermediate Similarity	NPC472495
0.8095	Intermediate Similarity	NPC471094
0.8095	Intermediate Similarity	NPC89860
0.8095	Intermediate Similarity	NPC469984
0.8095	Intermediate Similarity	NPC473410
0.8095	Intermediate Similarity	NPC189663
0.8081	Intermediate Similarity	NPC142352
0.8081	Intermediate Similarity	NPC41070
0.8081	Intermediate Similarity	NPC266431
0.8077	Intermediate Similarity	NPC138908
0.8077	Intermediate Similarity	NPC56656
0.8077	Intermediate Similarity	NPC103172
0.8077	Intermediate Similarity	NPC164600
0.8077	Intermediate Similarity	NPC200957
0.8058	Intermediate Similarity	NPC469985
0.8058	Intermediate Similarity	NPC470310
0.8041	Intermediate Similarity	NPC100313
0.8039	Intermediate Similarity	NPC471790
0.8039	Intermediate Similarity	NPC71706
0.8039	Intermediate Similarity	NPC252614
0.8037	Intermediate Similarity	NPC122339
0.8037	Intermediate Similarity	NPC329953
0.8037	Intermediate Similarity	NPC29505
0.8037	Intermediate Similarity	NPC470281
0.8021	Intermediate Similarity	NPC472739
0.802	Intermediate Similarity	NPC78427
0.802	Intermediate Similarity	NPC16911
0.8019	Intermediate Similarity	NPC118721
0.8019	Intermediate Similarity	NPC470615
0.8019	Intermediate Similarity	NPC469744
0.8019	Intermediate Similarity	NPC252679
0.8	Intermediate Similarity	NPC471042
0.8	Intermediate Similarity	NPC219353
0.8	Intermediate Similarity	NPC61071
0.8	Intermediate Similarity	NPC166993
0.7981	Intermediate Similarity	NPC137657
0.7979	Intermediate Similarity	NPC474233
0.7979	Intermediate Similarity	NPC475745
0.7979	Intermediate Similarity	NPC474482
0.7963	Intermediate Similarity	NPC471245
0.7963	Intermediate Similarity	NPC473303
0.7959	Intermediate Similarity	NPC470230
0.7959	Intermediate Similarity	NPC185936
0.7959	Intermediate Similarity	NPC168027
0.7957	Intermediate Similarity	NPC110780
0.7944	Intermediate Similarity	NPC471476

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 NPC288 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	2403
0.2-0.3	4178
0.3-0.4	1552
0.4-0.5	390
0.5-0.6	172
0.6-0.7	154
0.7-0.8	55
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7822	Intermediate Similarity	NPD5221	Approved
0.7822	Intermediate Similarity	NPD4697	Phase 3
0.7822	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD5222	Approved
0.7778	Intermediate Similarity	NPD8035	Phase 2
0.7778	Intermediate Similarity	NPD8034	Phase 2
0.7767	Intermediate Similarity	NPD5285	Approved
0.7767	Intermediate Similarity	NPD5286	Approved
0.7767	Intermediate Similarity	NPD4696	Approved
0.7745	Intermediate Similarity	NPD5173	Approved
0.7745	Intermediate Similarity	NPD4755	Approved
0.7692	Intermediate Similarity	NPD5223	Approved
0.7664	Intermediate Similarity	NPD5697	Approved
0.7619	Intermediate Similarity	NPD5224	Approved
0.7619	Intermediate Similarity	NPD5225	Approved
0.7619	Intermediate Similarity	NPD5211	Phase 2
0.7619	Intermediate Similarity	NPD5226	Approved
0.7619	Intermediate Similarity	NPD4633	Approved
0.76	Intermediate Similarity	NPD6079	Approved
0.7596	Intermediate Similarity	NPD4700	Approved
0.7593	Intermediate Similarity	NPD6881	Approved
0.7593	Intermediate Similarity	NPD6899	Approved
0.7593	Intermediate Similarity	NPD6011	Approved
0.7576	Intermediate Similarity	NPD5328	Approved
0.757	Intermediate Similarity	NPD7128	Approved
0.757	Intermediate Similarity	NPD6675	Approved
0.757	Intermediate Similarity	NPD5739	Approved
0.757	Intermediate Similarity	NPD6402	Approved
0.7547	Intermediate Similarity	NPD5174	Approved
0.7547	Intermediate Similarity	NPD5175	Approved
0.7545	Intermediate Similarity	NPD6649	Approved
0.7545	Intermediate Similarity	NPD6650	Approved
0.7526	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6372	Approved
0.7523	Intermediate Similarity	NPD6373	Approved
0.7523	Intermediate Similarity	NPD6013	Approved
0.7523	Intermediate Similarity	NPD6012	Approved
0.7523	Intermediate Similarity	NPD6014	Approved
0.75	Intermediate Similarity	NPD5701	Approved
0.7477	Intermediate Similarity	NPD5141	Approved
0.7455	Intermediate Similarity	NPD7102	Approved
0.7455	Intermediate Similarity	NPD6883	Approved
0.7455	Intermediate Similarity	NPD7290	Approved
0.7455	Intermediate Similarity	NPD4634	Approved
0.7449	Intermediate Similarity	NPD3618	Phase 1
0.7431	Intermediate Similarity	NPD7320	Approved
0.7387	Intermediate Similarity	NPD6847	Approved
0.7387	Intermediate Similarity	NPD6617	Approved
0.7387	Intermediate Similarity	NPD8130	Phase 1
0.7387	Intermediate Similarity	NPD6869	Approved
0.7383	Intermediate Similarity	NPD4754	Approved
0.7379	Intermediate Similarity	NPD4629	Approved
0.7379	Intermediate Similarity	NPD5210	Approved
0.7321	Intermediate Similarity	NPD6882	Approved
0.7321	Intermediate Similarity	NPD8297	Approved
0.732	Intermediate Similarity	NPD4788	Approved
0.7273	Intermediate Similarity	NPD4729	Approved
0.7273	Intermediate Similarity	NPD5128	Approved
0.7273	Intermediate Similarity	NPD4730	Approved
0.7248	Intermediate Similarity	NPD4768	Approved
0.7248	Intermediate Similarity	NPD4767	Approved
0.7238	Intermediate Similarity	NPD7902	Approved
0.7232	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6399	Phase 3
0.7184	Intermediate Similarity	NPD4202	Approved
0.7179	Intermediate Similarity	NPD6319	Approved
0.7179	Intermediate Similarity	NPD6054	Approved
0.717	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD5251	Approved
0.7143	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5250	Approved
0.7143	Intermediate Similarity	NPD5249	Phase 3
0.7143	Intermediate Similarity	NPD5169	Approved
0.7143	Intermediate Similarity	NPD5135	Approved
0.7143	Intermediate Similarity	NPD5248	Approved
0.7143	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD6274	Approved
0.7119	Intermediate Similarity	NPD6015	Approved
0.7119	Intermediate Similarity	NPD6016	Approved
0.7117	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5168	Approved
0.7115	Intermediate Similarity	NPD7748	Approved
0.7105	Intermediate Similarity	NPD4632	Approved
0.71	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7515	Phase 2
0.708	Intermediate Similarity	NPD5127	Approved
0.708	Intermediate Similarity	NPD5217	Approved
0.708	Intermediate Similarity	NPD5215	Approved
0.708	Intermediate Similarity	NPD5216	Approved
0.7071	Intermediate Similarity	NPD4786	Approved
0.7069	Intermediate Similarity	NPD6317	Approved
0.7059	Intermediate Similarity	NPD6370	Approved
0.7059	Intermediate Similarity	NPD5988	Approved
0.7059	Intermediate Similarity	NPD4753	Phase 2
0.7049	Intermediate Similarity	NPD7736	Approved
0.7041	Intermediate Similarity	NPD3667	Approved
0.7034	Intermediate Similarity	NPD6059	Approved
0.7021	Intermediate Similarity	NPD3703	Phase 2
0.7009	Intermediate Similarity	NPD6313	Approved
0.7009	Intermediate Similarity	NPD6314	Approved
0.7009	Intermediate Similarity	NPD6335	Approved
0.7	Intermediate Similarity	NPD8328	Phase 3
0.6983	Remote Similarity	NPD6868	Approved
0.6975	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7900	Approved
0.6952	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7100	Approved
0.6949	Remote Similarity	NPD7101	Approved
0.6942	Remote Similarity	NPD7492	Approved
0.6931	Remote Similarity	NPD5279	Phase 3
0.6923	Remote Similarity	NPD6009	Approved
0.6923	Remote Similarity	NPD7115	Discovery
0.6916	Remote Similarity	NPD6083	Phase 2
0.6916	Remote Similarity	NPD6084	Phase 2
0.69	Remote Similarity	NPD3666	Approved
0.69	Remote Similarity	NPD3133	Approved
0.69	Remote Similarity	NPD3665	Phase 1
0.6897	Remote Similarity	NPD5167	Approved
0.6885	Remote Similarity	NPD6616	Approved
0.6882	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6116	Phase 1
0.6863	Remote Similarity	NPD3573	Approved
0.6848	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7525	Registered
0.6833	Remote Similarity	NPD5983	Phase 2
0.6829	Remote Similarity	NPD7078	Approved
0.6796	Remote Similarity	NPD5737	Approved
0.6796	Remote Similarity	NPD6672	Approved
0.6786	Remote Similarity	NPD6008	Approved
0.678	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4789	Approved
0.6771	Remote Similarity	NPD6117	Approved
0.6733	Remote Similarity	NPD4197	Approved
0.6729	Remote Similarity	NPD5695	Phase 3
0.6721	Remote Similarity	NPD7604	Phase 2
0.6697	Remote Similarity	NPD7638	Approved
0.6694	Remote Similarity	NPD6909	Approved
0.6694	Remote Similarity	NPD6908	Approved
0.6694	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.664	Remote Similarity	NPD6033	Approved
0.6636	Remote Similarity	NPD7640	Approved
0.6636	Remote Similarity	NPD7639	Approved
0.6635	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6697	Approved
0.6633	Remote Similarity	NPD6114	Approved
0.6633	Remote Similarity	NPD6115	Approved
0.6633	Remote Similarity	NPD6118	Approved
0.6633	Remote Similarity	NPD3617	Approved
0.6613	Remote Similarity	NPD6336	Discontinued
0.6604	Remote Similarity	NPD6411	Approved
0.6602	Remote Similarity	NPD5690	Phase 2
0.6587	Remote Similarity	NPD7319	Approved
0.6579	Remote Similarity	NPD6412	Phase 2
0.6569	Remote Similarity	NPD3668	Phase 3
0.6562	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4225	Approved
0.6535	Remote Similarity	NPD4221	Approved
0.6535	Remote Similarity	NPD4223	Phase 3
0.6525	Remote Similarity	NPD8133	Approved
0.6518	Remote Similarity	NPD5091	Approved
0.6489	Remote Similarity	NPD3698	Phase 2
0.6481	Remote Similarity	NPD5282	Discontinued
0.648	Remote Similarity	NPD7507	Approved
0.6442	Remote Similarity	NPD7334	Approved
0.6442	Remote Similarity	NPD6409	Approved
0.6442	Remote Similarity	NPD5330	Approved
0.6442	Remote Similarity	NPD4694	Approved
0.6442	Remote Similarity	NPD6684	Approved
0.6442	Remote Similarity	NPD7146	Approved
0.6442	Remote Similarity	NPD7521	Approved
0.6442	Remote Similarity	NPD5280	Approved
0.6423	Remote Similarity	NPD6921	Approved
0.6422	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4244	Approved
0.6421	Remote Similarity	NPD4245	Approved
0.6415	Remote Similarity	NPD6673	Approved
0.6415	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6904	Approved
0.6415	Remote Similarity	NPD6080	Approved
0.6415	Remote Similarity	NPD6101	Approved
0.6413	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7645	Phase 2
0.6383	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5360	Phase 3
0.6354	Remote Similarity	NPD6081	Approved
0.6327	Remote Similarity	NPD3702	Approved
0.6325	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6903	Approved
0.6316	Remote Similarity	NPD6333	Approved
0.6316	Remote Similarity	NPD6334	Approved
0.63	Remote Similarity	NPD3671	Phase 1
0.6296	Remote Similarity	NPD5281	Approved
0.6296	Remote Similarity	NPD5693	Phase 1
0.6296	Remote Similarity	NPD5284	Approved
0.6286	Remote Similarity	NPD4693	Phase 3
0.6286	Remote Similarity	NPD4138	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