NPASS Compound

Structure

NPC229752 OpenBabel07101719132D 29 34 0 0 1 0 0 0 0 0999 V2000 -2.6843 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9561 -3.6109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5886 -0.7740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1078 0.0586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8216 -0.2813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4220 -0.8467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2518 -1.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6271 -1.2073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8127 -0.5601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7887 -3.1302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6287 0.3836 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7308 -0.8868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1234 -1.2073 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2518 -0.5573 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9721 -1.0267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1617 -0.1335 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6743 0.5002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1671 -0.2288 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6271 -0.7740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1234 -0.7740 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2685 -0.3715 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2692 -0.0882 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6213 -3.6109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8555 -1.9811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8051 0.5810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1786 0.2237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7887 -2.1688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0781 0.3383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 23 2 0 0 0 0 10 27 1 0 0 0 0 11 5 1 6 0 0 0 11 17 1 0 0 0 0 12 20 1 6 0 0 0 12 21 1 0 0 0 0 13 20 1 6 0 0 0 13 27 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 6 0 0 0 15 21 1 0 0 0 0 15 24 2 0 0 0 0 16 22 1 1 0 0 0 16 25 1 0 0 0 0 17 21 1 1 0 0 0 17 28 1 0 0 0 0 18 20 1 6 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 21 22 1 0 0 0 0 22 26 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.18
Volume:	391.352
LogP:	2.104
LogD:	1.795
LogS:	-4.728
# Rotatable Bonds:	2
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.502
Synthetic Accessibility Score:	7.438
Fsp3:	0.818
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:	-4.973
MDCK Permeability:	2.5933992219506763e-05
Pgp-inhibitor:	0.334
Pgp-substrate:	0.185
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.766

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.527
Plasma Protein Binding (PPB):	53.9229736328125%
Volume Distribution (VD):	1.118
Pgp-substrate:	61.14863204956055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.677
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.582
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	2.691
Half-life (T1/2):	0.203

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.105
Drug-inuced Liver Injury (DILI):	0.1
AMES Toxicity:	0.326
Rat Oral Acute Toxicity:	0.954
Maximum Recommended Daily Dose:	0.603
Skin Sensitization:	0.59
Carcinogencity:	0.892
Eye Corrosion:	0.008
Eye Irritation:	0.021
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC229752

Natural Product ID:	NPC229752
*Common Name:**	Isoadenolin B
IUPAC Name:	n.a.
Synonyms:	isoadenolin B
Standard InCHIKey:	OWZOEAKQPTYTKK-KKKROVPOSA-N
Standard InCHI:	InChI=1S/C22H28O7/c1-9-11-5-6-12-20-13(27-10(2)23)7-8-19(3,4)14(20)16(25)22(26)21(12,15(9)24)17(11)28-18(20)29-22/h11-14,16-18,25-26H,1,5-8H2,2-4H3/t11-,12-,13-,14+,16-,17-,18-,20-,21-,22+/m0/s1
SMILES:	C=C1[C@@H]2CC[C@H]3[C@]45[C@H](CCC(C)(C)[C@H]4[C@@H]([C@@]4([C@@]3(C1=O)[C@H]2O[C@H]5O4)O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1802167
PubChem CID:	56669880
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
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21534539]
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	aerial parts	Shangrila, Yunnan Province, China	2008-AUG	PMID[21534539]
NPO18055	Isodon adenolomus	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[566636]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[566636]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[566636]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[566636]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[566636]

☑ 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 NPC229752 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	307
0.1-0.2	2085
0.2-0.3	6094
0.3-0.4	10480
0.4-0.5	10213
0.5-0.6	6443
0.6-0.7	3889
0.7-0.8	2122
0.8-0.85	889
0.85-0.9	102
0.9-0.95	32
0.95-1	41

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC78836
0.9811	High Similarity	NPC94141
0.972	High Similarity	NPC17165
0.9717	High Similarity	NPC157929
0.963	High Similarity	NPC88945
0.9626	High Similarity	NPC132668
0.9623	High Similarity	NPC63244
0.9533	High Similarity	NPC471244
0.9533	High Similarity	NPC145625
0.9528	High Similarity	NPC471476
0.9439	High Similarity	NPC122339
0.9439	High Similarity	NPC213320
0.9434	High Similarity	NPC102741
0.9364	High Similarity	NPC473304
0.9352	High Similarity	NPC474927
0.9352	High Similarity	NPC473397
0.9352	High Similarity	NPC473352
0.9352	High Similarity	NPC471245
0.9352	High Similarity	NPC473303
0.9346	High Similarity	NPC471093
0.9346	High Similarity	NPC473324
0.934	High Similarity	NPC189663
0.934	High Similarity	NPC469984
0.934	High Similarity	NPC471094
0.934	High Similarity	NPC473410
0.934	High Similarity	NPC89860
0.9266	High Similarity	NPC471248
0.9259	High Similarity	NPC29505
0.9252	High Similarity	NPC252679
0.9252	High Similarity	NPC118721
0.9245	High Similarity	NPC471474
0.9167	High Similarity	NPC474786
0.9167	High Similarity	NPC85391
0.9167	High Similarity	NPC137104
0.9167	High Similarity	NPC320383
0.9159	High Similarity	NPC63841
0.9159	High Similarity	NPC55973
0.9151	High Similarity	NPC130511
0.9151	High Similarity	NPC307660
0.9151	High Similarity	NPC56656
0.9091	High Similarity	NPC471252
0.9083	High Similarity	NPC329953
0.9074	High Similarity	NPC131903
0.9074	High Similarity	NPC469744
0.9074	High Similarity	NPC274827
0.9065	High Similarity	NPC186054
0.9065	High Similarity	NPC471461
0.9065	High Similarity	NPC469746
0.9065	High Similarity	NPC67745
0.9057	High Similarity	NPC202793
0.9009	High Similarity	NPC243354
0.8981	High Similarity	NPC232133
0.8981	High Similarity	NPC469733
0.8981	High Similarity	NPC469729
0.8972	High Similarity	NPC12823
0.8919	High Similarity	NPC194273
0.8909	High Similarity	NPC56025
0.8899	High Similarity	NPC469983
0.8785	High Similarity	NPC139347
0.8774	High Similarity	NPC14634
0.8739	High Similarity	NPC471243
0.8716	High Similarity	NPC88833
0.8716	High Similarity	NPC96333
0.8704	High Similarity	NPC474558
0.8692	High Similarity	NPC475803
0.8692	High Similarity	NPC309388
0.8661	High Similarity	NPC207845
0.8661	High Similarity	NPC472719
0.8649	High Similarity	NPC98069
0.8649	High Similarity	NPC49730
0.8636	High Similarity	NPC231278
0.8636	High Similarity	NPC273155
0.8636	High Similarity	NPC112895
0.8636	High Similarity	NPC218123
0.8624	High Similarity	NPC103172
0.8624	High Similarity	NPC4115
0.8624	High Similarity	NPC164600
0.8611	High Similarity	NPC209298
0.8611	High Similarity	NPC277074
0.8596	High Similarity	NPC472718
0.8584	High Similarity	NPC146563
0.8584	High Similarity	NPC320118
0.8584	High Similarity	NPC73986
0.8571	High Similarity	NPC11035
0.8571	High Similarity	NPC274833
0.8571	High Similarity	NPC273962
0.8547	High Similarity	NPC470478
0.8545	High Similarity	NPC61071
0.8545	High Similarity	NPC166993
0.8532	High Similarity	NPC101842
0.8522	High Similarity	NPC156651
0.8509	High Similarity	NPC54395
0.8505	High Similarity	NPC470388
0.8496	Intermediate Similarity	NPC470543
0.8487	Intermediate Similarity	NPC248202
0.8455	Intermediate Similarity	NPC200957
0.8455	Intermediate Similarity	NPC138908
0.844	Intermediate Similarity	NPC107385
0.844	Intermediate Similarity	NPC122811
0.844	Intermediate Similarity	NPC87927
0.8435	Intermediate Similarity	NPC469823
0.8435	Intermediate Similarity	NPC137414
0.8435	Intermediate Similarity	NPC469820
0.8426	Intermediate Similarity	NPC163963
0.8426	Intermediate Similarity	NPC52899
0.8426	Intermediate Similarity	NPC471790
0.8426	Intermediate Similarity	NPC289148
0.8417	Intermediate Similarity	NPC174367
0.8417	Intermediate Similarity	NPC47113
0.8411	Intermediate Similarity	NPC474793
0.8407	Intermediate Similarity	NPC1876
0.8407	Intermediate Similarity	NPC275668
0.8407	Intermediate Similarity	NPC91838
0.8407	Intermediate Similarity	NPC240734
0.8407	Intermediate Similarity	NPC204392
0.8393	Intermediate Similarity	NPC91583
0.8393	Intermediate Similarity	NPC240125
0.8393	Intermediate Similarity	NPC51947
0.8393	Intermediate Similarity	NPC473844
0.8393	Intermediate Similarity	NPC8431
0.839	Intermediate Similarity	NPC475182
0.8364	Intermediate Similarity	NPC301787
0.8364	Intermediate Similarity	NPC13149
0.8362	Intermediate Similarity	NPC309433
0.8362	Intermediate Similarity	NPC470171
0.8362	Intermediate Similarity	NPC477252
0.8362	Intermediate Similarity	NPC218970
0.8349	Intermediate Similarity	NPC246736
0.8349	Intermediate Similarity	NPC76866
0.8349	Intermediate Similarity	NPC286519
0.8349	Intermediate Similarity	NPC304832
0.8349	Intermediate Similarity	NPC214946
0.8349	Intermediate Similarity	NPC88203
0.8349	Intermediate Similarity	NPC148628
0.8333	Intermediate Similarity	NPC469841
0.8333	Intermediate Similarity	NPC243572
0.8333	Intermediate Similarity	NPC469842
0.8333	Intermediate Similarity	NPC287676
0.8333	Intermediate Similarity	NPC130229
0.8319	Intermediate Similarity	NPC130302
0.8319	Intermediate Similarity	NPC156789
0.8319	Intermediate Similarity	NPC98633
0.8304	Intermediate Similarity	NPC88744
0.8291	Intermediate Similarity	NPC469822
0.8288	Intermediate Similarity	NPC222833
0.8288	Intermediate Similarity	NPC285927
0.8273	Intermediate Similarity	NPC216114
0.8273	Intermediate Similarity	NPC96217
0.8261	Intermediate Similarity	NPC102619
0.8257	Intermediate Similarity	NPC236585
0.8257	Intermediate Similarity	NPC148279
0.8257	Intermediate Similarity	NPC46848
0.8257	Intermediate Similarity	NPC252614
0.825	Intermediate Similarity	NPC160084
0.8246	Intermediate Similarity	NPC272242
0.8246	Intermediate Similarity	NPC471251
0.8241	Intermediate Similarity	NPC16911
0.8241	Intermediate Similarity	NPC78427
0.8241	Intermediate Similarity	NPC471038
0.823	Intermediate Similarity	NPC471250
0.8226	Intermediate Similarity	NPC473805
0.8226	Intermediate Similarity	NPC473519
0.8224	Intermediate Similarity	NPC13949
0.822	Intermediate Similarity	NPC473401
0.822	Intermediate Similarity	NPC161738
0.8214	Intermediate Similarity	NPC287269
0.8214	Intermediate Similarity	NPC470166
0.8211	Intermediate Similarity	NPC476966
0.8205	Intermediate Similarity	NPC300419
0.8198	Intermediate Similarity	NPC244247
0.8198	Intermediate Similarity	NPC84928
0.8198	Intermediate Similarity	NPC470167
0.8198	Intermediate Similarity	NPC98603
0.819	Intermediate Similarity	NPC469821
0.819	Intermediate Similarity	NPC475633
0.819	Intermediate Similarity	NPC473882
0.8182	Intermediate Similarity	NPC7850
0.8182	Intermediate Similarity	NPC30188
0.8182	Intermediate Similarity	NPC6615
0.8182	Intermediate Similarity	NPC471963
0.8182	Intermediate Similarity	NPC470172
0.8182	Intermediate Similarity	NPC177820
0.8182	Intermediate Similarity	NPC473474
0.8182	Intermediate Similarity	NPC247315
0.8182	Intermediate Similarity	NPC470477
0.8182	Intermediate Similarity	NPC275990
0.8182	Intermediate Similarity	NPC471962
0.8174	Intermediate Similarity	NPC205534
0.8174	Intermediate Similarity	NPC233003
0.8167	Intermediate Similarity	NPC213952
0.8167	Intermediate Similarity	NPC162574
0.8167	Intermediate Similarity	NPC471965
0.8165	Intermediate Similarity	NPC267921
0.8165	Intermediate Similarity	NPC127408
0.8165	Intermediate Similarity	NPC291785
0.816	Intermediate Similarity	NPC102015
0.8158	Intermediate Similarity	NPC124053
0.8158	Intermediate Similarity	NPC255655
0.8151	Intermediate Similarity	NPC471406
0.8151	Intermediate Similarity	NPC108072

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 NPC229752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	2449
0.2-0.3	3902
0.3-0.4	1589
0.4-0.5	463
0.5-0.6	262
0.6-0.7	134
0.7-0.8	41
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
0.8103	Intermediate Similarity	NPD8133	Approved
0.8099	Intermediate Similarity	NPD8328	Phase 3
0.8051	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7736	Approved
0.7778	Intermediate Similarity	NPD7319	Approved
0.7739	Intermediate Similarity	NPD6412	Phase 2
0.7724	Intermediate Similarity	NPD6370	Approved
0.7719	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7507	Approved
0.7619	Intermediate Similarity	NPD8293	Discontinued
0.76	Intermediate Similarity	NPD7492	Approved
0.7561	Intermediate Similarity	NPD6319	Approved
0.7561	Intermediate Similarity	NPD6054	Approved
0.754	Intermediate Similarity	NPD6616	Approved
0.7521	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD6015	Approved
0.748	Intermediate Similarity	NPD7078	Approved
0.7459	Intermediate Similarity	NPD6009	Approved
0.744	Intermediate Similarity	NPD5988	Approved
0.7419	Intermediate Similarity	NPD8294	Approved
0.7419	Intermediate Similarity	NPD6059	Approved
0.7419	Intermediate Similarity	NPD8377	Approved
0.7373	Intermediate Similarity	NPD6686	Approved
0.736	Intermediate Similarity	NPD8515	Approved
0.736	Intermediate Similarity	NPD8513	Phase 3
0.736	Intermediate Similarity	NPD8033	Approved
0.736	Intermediate Similarity	NPD8296	Approved
0.736	Intermediate Similarity	NPD8380	Approved
0.736	Intermediate Similarity	NPD8378	Approved
0.736	Intermediate Similarity	NPD8517	Approved
0.736	Intermediate Similarity	NPD8516	Approved
0.736	Intermediate Similarity	NPD8335	Approved
0.736	Intermediate Similarity	NPD8379	Approved
0.7355	Intermediate Similarity	NPD4632	Approved
0.7273	Intermediate Similarity	NPD6882	Approved
0.72	Intermediate Similarity	NPD7516	Approved
0.7177	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD5697	Approved
0.7131	Intermediate Similarity	NPD8297	Approved
0.712	Intermediate Similarity	NPD7328	Approved
0.712	Intermediate Similarity	NPD7327	Approved
0.7107	Intermediate Similarity	NPD4634	Approved
0.7087	Intermediate Similarity	NPD7503	Approved
0.7083	Intermediate Similarity	NPD6899	Approved
0.7083	Intermediate Similarity	NPD6881	Approved
0.7059	Intermediate Similarity	NPD7128	Approved
0.7059	Intermediate Similarity	NPD5739	Approved
0.7059	Intermediate Similarity	NPD6402	Approved
0.7059	Intermediate Similarity	NPD6008	Approved
0.7059	Intermediate Similarity	NPD6675	Approved
0.7054	Intermediate Similarity	NPD8035	Phase 2
0.7054	Intermediate Similarity	NPD8034	Phase 2
0.7049	Intermediate Similarity	NPD6649	Approved
0.7049	Intermediate Similarity	NPD6650	Approved
0.7025	Intermediate Similarity	NPD6012	Approved
0.7025	Intermediate Similarity	NPD6373	Approved
0.7025	Intermediate Similarity	NPD6014	Approved
0.7025	Intermediate Similarity	NPD6013	Approved
0.7025	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD5701	Approved
0.6967	Remote Similarity	NPD7102	Approved
0.6967	Remote Similarity	NPD6883	Approved
0.6967	Remote Similarity	NPD7290	Approved
0.6953	Remote Similarity	NPD5983	Phase 2
0.6942	Remote Similarity	NPD7320	Approved
0.6942	Remote Similarity	NPD6011	Approved
0.6911	Remote Similarity	NPD6847	Approved
0.6911	Remote Similarity	NPD6617	Approved
0.6911	Remote Similarity	NPD8130	Phase 1
0.6911	Remote Similarity	NPD6869	Approved
0.6894	Remote Similarity	NPD6033	Approved
0.6846	Remote Similarity	NPD7604	Phase 2
0.6842	Remote Similarity	NPD8171	Discontinued
0.6842	Remote Similarity	NPD6399	Phase 3
0.6838	Remote Similarity	NPD4225	Approved
0.6822	Remote Similarity	NPD6921	Approved
0.6818	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5285	Approved
0.678	Remote Similarity	NPD4696	Approved
0.678	Remote Similarity	NPD5286	Approved
0.6752	Remote Similarity	NPD7902	Approved
0.6752	Remote Similarity	NPD4755	Approved
0.6748	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6336	Discontinued
0.6718	Remote Similarity	NPD6067	Discontinued
0.6693	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.664	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4700	Approved
0.6638	Remote Similarity	NPD7748	Approved
0.6612	Remote Similarity	NPD5174	Approved
0.6612	Remote Similarity	NPD5175	Approved
0.6609	Remote Similarity	NPD7515	Phase 2
0.6609	Remote Similarity	NPD6079	Approved
0.6583	Remote Similarity	NPD5223	Approved
0.6579	Remote Similarity	NPD5328	Approved
0.656	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5141	Approved
0.6555	Remote Similarity	NPD7638	Approved
0.6538	Remote Similarity	NPD7101	Approved
0.6538	Remote Similarity	NPD7100	Approved
0.6525	Remote Similarity	NPD5221	Approved
0.6525	Remote Similarity	NPD4697	Phase 3
0.6525	Remote Similarity	NPD5222	Approved
0.6525	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6317	Approved
0.6508	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7640	Approved
0.65	Remote Similarity	NPD7639	Approved
0.6496	Remote Similarity	NPD7900	Approved
0.6496	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6083	Phase 2
0.6471	Remote Similarity	NPD6084	Phase 2
0.6471	Remote Similarity	NPD5173	Approved
0.6466	Remote Similarity	NPD6411	Approved
0.6462	Remote Similarity	NPD6314	Approved
0.6462	Remote Similarity	NPD6335	Approved
0.6462	Remote Similarity	NPD6313	Approved
0.646	Remote Similarity	NPD3618	Phase 1
0.6455	Remote Similarity	NPD1779	Approved
0.6455	Remote Similarity	NPD1780	Approved
0.6446	Remote Similarity	NPD1700	Approved
0.6444	Remote Similarity	NPD8074	Phase 3
0.6439	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6940	Discontinued
0.6429	Remote Similarity	NPD6371	Approved
0.6423	Remote Similarity	NPD5956	Approved
0.6417	Remote Similarity	NPD5696	Approved
0.641	Remote Similarity	NPD4202	Approved
0.6404	Remote Similarity	NPD3573	Approved
0.64	Remote Similarity	NPD4730	Approved
0.64	Remote Similarity	NPD5128	Approved
0.64	Remote Similarity	NPD4729	Approved
0.6371	Remote Similarity	NPD4767	Approved
0.6371	Remote Similarity	NPD4768	Approved
0.6341	Remote Similarity	NPD4754	Approved
0.6339	Remote Similarity	NPD4788	Approved
0.6339	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD3669	Approved
0.633	Remote Similarity	NPD6115	Approved
0.633	Remote Similarity	NPD6697	Approved
0.633	Remote Similarity	NPD6114	Approved
0.633	Remote Similarity	NPD6118	Approved
0.632	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6909	Approved
0.6316	Remote Similarity	NPD6908	Approved
0.6308	Remote Similarity	NPD6868	Approved
0.6303	Remote Similarity	NPD5695	Phase 3
0.6299	Remote Similarity	NPD5248	Approved
0.6299	Remote Similarity	NPD5247	Approved
0.6299	Remote Similarity	NPD5250	Approved
0.6299	Remote Similarity	NPD5251	Approved
0.6299	Remote Similarity	NPD5249	Phase 3
0.6293	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6101	Approved
0.6283	Remote Similarity	NPD4786	Approved
0.6277	Remote Similarity	NPD8337	Approved
0.6277	Remote Similarity	NPD8336	Approved
0.625	Remote Similarity	NPD5217	Approved
0.625	Remote Similarity	NPD5215	Approved
0.625	Remote Similarity	NPD5216	Approved
0.625	Remote Similarity	NPD3667	Approved
0.6239	Remote Similarity	NPD6116	Phase 1
0.6224	Remote Similarity	NPD6333	Approved
0.6224	Remote Similarity	NPD6334	Approved
0.6214	Remote Similarity	NPD8338	Approved
0.6207	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD3703	Phase 2
0.6202	Remote Similarity	NPD6053	Discontinued
0.6174	Remote Similarity	NPD7521	Approved
0.6174	Remote Similarity	NPD7146	Approved
0.6174	Remote Similarity	NPD5330	Approved
0.6174	Remote Similarity	NPD6684	Approved
0.6174	Remote Similarity	NPD6409	Approved
0.6174	Remote Similarity	NPD7334	Approved
0.6172	Remote Similarity	NPD5169	Approved
0.6172	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD5135	Approved
0.6167	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD5210	Approved
0.6167	Remote Similarity	NPD4629	Approved
0.6167	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.616	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.616	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4753	Phase 2
0.6148	Remote Similarity	NPD8080	Discontinued
0.6147	Remote Similarity	NPD6117	Approved
0.614	Remote Similarity	NPD3665	Phase 1
0.614	Remote Similarity	NPD3133	Approved
0.614	Remote Similarity	NPD3666	Approved
0.6136	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD5779	Approved
0.6134	Remote Similarity	NPD5778	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