NPASS Compound

Structure

CID190294 OpenBabel06191715572D 29 30 0 0 1 0 0 0 0 0999 V2000 0.7254 4.4924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3077 5.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0594 -2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2319 2.5772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7624 1.7722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7843 1.5642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2618 -1.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0050 -0.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 1.8563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7199 4.3879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2673 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0933 2.5153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9456 1.7518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2129 0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1266 3.4744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8061 1.3563 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4023 3.4664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2074 0.5473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1211 3.3698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 2.6654 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 4.1151 2.3074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 10 1 0 0 0 0 4 12 2 0 0 0 0 5 13 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 15 1 0 0 0 0 9 14 1 0 0 0 0 9 21 1 0 0 0 0 10 19 1 0 0 0 0 11 3 1 6 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 22 2 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 14 27 1 1 0 0 0 15 21 1 0 0 0 0 15 23 2 0 0 0 0 16 12 1 6 0 0 0 16 18 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 6 0 0 0 18 28 1 1 0 0 0 19 25 2 0 0 0 0 19 27 1 0 0 0 0 20 26 2 0 0 0 0 20 28 1 0 0 0 0 21 6 1 6 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.18
Volume:	409.162
LogP:	1.553
LogD:	1.712
LogS:	-2.71
# Rotatable Bonds:	5
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	5.168
Fsp3:	0.619
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:	-4.913
MDCK Permeability:	8.412671013502404e-05
Pgp-inhibitor:	0.07
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.44
20% Bioavailability (F20%):	0.742
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.659
Plasma Protein Binding (PPB):	57.4312744140625%
Volume Distribution (VD):	0.45
Pgp-substrate:	34.15974044799805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.608
CYP2C9-inhibitor:	0.209
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.34
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	8.807
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.879
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.131
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.483
Carcinogencity:	0.093
Eye Corrosion:	0.025
Eye Irritation:	0.184
Respiratory Toxicity:	0.455

Download Data

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

Natural Product: NPC190294

Natural Product ID:	NPC190294
*Common Name:**	Lychnostatin 1
IUPAC Name:	[(3aR,4S,6R,10S,11S,11aS)-6-acetyloxy-11-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,8,9,10,11,11a-octahydrocyclodeca[b]furan-4-yl] 2-methylprop-2-enoate
Synonyms:	Lychnostatin 1
Standard InCHIKey:	OLFNVRXCVQOTPN-ZBTOSGMISA-N
Standard InCHI:	InChI=1S/C21H28O8/c1-10(2)19(25)27-14-9-21(6,29-13(5)22)15(23)8-7-11(3)17(24)18-16(14)12(4)20(26)28-18/h11,14,16-18,24H,1,4,7-9H2,2-3,5-6H3/t11-,14-,16+,17-,18-,21+/m0/s1
SMILES:	C=C(C)C(=O)O[C@H]1C[C@](C)(C(=O)CC[C@H](C)[C@@H]([C@@H]2[C@@H]1C(=C)C(=O)O2)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457258
PubChem CID:	131021
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
NPO30091	Lychnophora antillana	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[2380713]
NPO30091	Lychnophora antillana	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[2380713]

☑ 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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.0	ug ml-1	PMID[496977]

☑ 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 NPC190294 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	1858
0.2-0.3	5995
0.3-0.4	11613
0.4-0.5	12348
0.5-0.6	7066
0.6-0.7	2815
0.7-0.8	643
0.8-0.85	68
0.85-0.9	19
0.9-0.95	11
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC323421
0.9667	High Similarity	NPC328562
0.9556	High Similarity	NPC31645
0.9556	High Similarity	NPC39859
0.9556	High Similarity	NPC76862
0.9556	High Similarity	NPC158416
0.9556	High Similarity	NPC470883
0.9255	High Similarity	NPC320019
0.9255	High Similarity	NPC324017
0.9149	High Similarity	NPC15993
0.913	High Similarity	NPC476009
0.9101	High Similarity	NPC173926
0.8947	High Similarity	NPC201718
0.8901	High Similarity	NPC70251
0.8901	High Similarity	NPC475881
0.8889	High Similarity	NPC474951
0.8889	High Similarity	NPC92974
0.8876	High Similarity	NPC186148
0.8851	High Similarity	NPC128429
0.8817	High Similarity	NPC475900
0.8778	High Similarity	NPC177629
0.8778	High Similarity	NPC58219
0.875	High Similarity	NPC476270
0.875	High Similarity	NPC47880
0.8696	High Similarity	NPC184463
0.8696	High Similarity	NPC329952
0.8667	High Similarity	NPC5130
0.866	High Similarity	NPC149371
0.8617	High Similarity	NPC36954
0.8602	High Similarity	NPC475912
0.8602	High Similarity	NPC212486
0.8602	High Similarity	NPC476300
0.8587	High Similarity	NPC65359
0.8571	High Similarity	NPC202672
0.8556	High Similarity	NPC474762
0.8556	High Similarity	NPC475019
0.8556	High Similarity	NPC474949
0.8556	High Similarity	NPC476015
0.8542	High Similarity	NPC471144
0.8542	High Similarity	NPC474213
0.8539	High Similarity	NPC3464
0.8539	High Similarity	NPC151176
0.8539	High Similarity	NPC474780
0.8539	High Similarity	NPC475963
0.85	High Similarity	NPC477513
0.8495	Intermediate Similarity	NPC30515
0.8495	Intermediate Similarity	NPC208886
0.8495	Intermediate Similarity	NPC12172
0.8478	Intermediate Similarity	NPC307411
0.8469	Intermediate Similarity	NPC474747
0.8454	Intermediate Similarity	NPC475949
0.8444	Intermediate Similarity	NPC329749
0.8444	Intermediate Similarity	NPC47958
0.8444	Intermediate Similarity	NPC149725
0.8444	Intermediate Similarity	NPC304509
0.8421	Intermediate Similarity	NPC14961
0.8421	Intermediate Similarity	NPC270013
0.8404	Intermediate Similarity	NPC179746
0.8404	Intermediate Similarity	NPC81419
0.8387	Intermediate Similarity	NPC51004
0.8387	Intermediate Similarity	NPC206614
0.8387	Intermediate Similarity	NPC474323
0.8384	Intermediate Similarity	NPC475945
0.8384	Intermediate Similarity	NPC472755
0.8384	Intermediate Similarity	NPC475871
0.8367	Intermediate Similarity	NPC474339
0.8367	Intermediate Similarity	NPC164598
0.8333	Intermediate Similarity	NPC476315
0.8316	Intermediate Similarity	NPC474035
0.8316	Intermediate Similarity	NPC81386
0.8298	Intermediate Similarity	NPC469627
0.8283	Intermediate Similarity	NPC471148
0.8283	Intermediate Similarity	NPC472754
0.8261	Intermediate Similarity	NPC190753
0.8247	Intermediate Similarity	NPC471150
0.8247	Intermediate Similarity	NPC474313
0.8229	Intermediate Similarity	NPC163228
0.8211	Intermediate Similarity	NPC162205
0.8211	Intermediate Similarity	NPC273579
0.8211	Intermediate Similarity	NPC288240
0.8211	Intermediate Similarity	NPC295204
0.8191	Intermediate Similarity	NPC474761
0.8191	Intermediate Similarity	NPC476004
0.8191	Intermediate Similarity	NPC473619
0.8182	Intermediate Similarity	NPC472753
0.8182	Intermediate Similarity	NPC474742
0.8182	Intermediate Similarity	NPC110443
0.8182	Intermediate Similarity	NPC46998
0.8182	Intermediate Similarity	NPC133907
0.8182	Intermediate Similarity	NPC128733
0.8182	Intermediate Similarity	NPC185141
0.8163	Intermediate Similarity	NPC473326
0.8155	Intermediate Similarity	NPC38154
0.8152	Intermediate Similarity	NPC470242
0.8144	Intermediate Similarity	NPC279621
0.8144	Intermediate Similarity	NPC473859
0.8132	Intermediate Similarity	NPC138647
0.8132	Intermediate Similarity	NPC470238
0.8125	Intermediate Similarity	NPC57405
0.8125	Intermediate Similarity	NPC303942
0.8119	Intermediate Similarity	NPC474741
0.8119	Intermediate Similarity	NPC472748
0.8119	Intermediate Similarity	NPC472756
0.8105	Intermediate Similarity	NPC473321
0.8085	Intermediate Similarity	NPC151770
0.8085	Intermediate Similarity	NPC474032
0.8081	Intermediate Similarity	NPC288876
0.8065	Intermediate Similarity	NPC118601
0.8041	Intermediate Similarity	NPC475659
0.8041	Intermediate Similarity	NPC471142
0.8039	Intermediate Similarity	NPC472749
0.8039	Intermediate Similarity	NPC474101
0.8039	Intermediate Similarity	NPC472751
0.802	Intermediate Similarity	NPC472747
0.802	Intermediate Similarity	NPC475873
0.802	Intermediate Similarity	NPC472750
0.8	Intermediate Similarity	NPC329857
0.8	Intermediate Similarity	NPC475748
0.8	Intermediate Similarity	NPC469718
0.8	Intermediate Similarity	NPC264477
0.8	Intermediate Similarity	NPC477511
0.7979	Intermediate Similarity	NPC473715
0.7979	Intermediate Similarity	NPC178875
0.7959	Intermediate Similarity	NPC17585
0.7957	Intermediate Similarity	NPC162071
0.7941	Intermediate Similarity	NPC100487
0.7938	Intermediate Similarity	NPC474247
0.7938	Intermediate Similarity	NPC121825
0.7938	Intermediate Similarity	NPC71589
0.7917	Intermediate Similarity	NPC20713
0.79	Intermediate Similarity	NPC471381
0.79	Intermediate Similarity	NPC186861
0.7889	Intermediate Similarity	NPC474981
0.7879	Intermediate Similarity	NPC471140
0.7872	Intermediate Similarity	NPC231889
0.7872	Intermediate Similarity	NPC179659
0.7872	Intermediate Similarity	NPC248602
0.7864	Intermediate Similarity	NPC44004
0.7857	Intermediate Similarity	NPC474947
0.7857	Intermediate Similarity	NPC471141
0.7857	Intermediate Similarity	NPC472873
0.7849	Intermediate Similarity	NPC21469
0.7843	Intermediate Similarity	NPC473148
0.7843	Intermediate Similarity	NPC4620
0.7835	Intermediate Similarity	NPC475302
0.7835	Intermediate Similarity	NPC125674
0.7835	Intermediate Similarity	NPC469645
0.7835	Intermediate Similarity	NPC469692
0.7835	Intermediate Similarity	NPC475838
0.7835	Intermediate Similarity	NPC475788
0.7835	Intermediate Similarity	NPC228451
0.7826	Intermediate Similarity	NPC11620
0.7826	Intermediate Similarity	NPC257358
0.7826	Intermediate Similarity	NPC474472
0.7822	Intermediate Similarity	NPC473332
0.7812	Intermediate Similarity	NPC179394
0.7812	Intermediate Similarity	NPC144133
0.7812	Intermediate Similarity	NPC475855
0.78	Intermediate Similarity	NPC187268
0.7789	Intermediate Similarity	NPC281516
0.7789	Intermediate Similarity	NPC217983
0.7789	Intermediate Similarity	NPC207114
0.7789	Intermediate Similarity	NPC153805
0.7788	Intermediate Similarity	NPC474421
0.7788	Intermediate Similarity	NPC324327
0.7788	Intermediate Similarity	NPC326994
0.7788	Intermediate Similarity	NPC72813
0.7788	Intermediate Similarity	NPC194620
0.7778	Intermediate Similarity	NPC230800
0.7778	Intermediate Similarity	NPC91771
0.7778	Intermediate Similarity	NPC477921
0.7778	Intermediate Similarity	NPC142529
0.7767	Intermediate Similarity	NPC477510
0.7767	Intermediate Similarity	NPC471143
0.7767	Intermediate Similarity	NPC220964
0.7767	Intermediate Similarity	NPC203659
0.7767	Intermediate Similarity	NPC475676
0.7766	Intermediate Similarity	NPC469626
0.7766	Intermediate Similarity	NPC236692
0.7766	Intermediate Similarity	NPC309757
0.7766	Intermediate Similarity	NPC475491
0.7755	Intermediate Similarity	NPC473331
0.7755	Intermediate Similarity	NPC473330
0.7755	Intermediate Similarity	NPC473316
0.7745	Intermediate Similarity	NPC225353
0.7745	Intermediate Similarity	NPC303653
0.7745	Intermediate Similarity	NPC291500
0.7745	Intermediate Similarity	NPC80144
0.7745	Intermediate Similarity	NPC189609
0.7745	Intermediate Similarity	NPC197835
0.7745	Intermediate Similarity	NPC140591
0.7736	Intermediate Similarity	NPC5103
0.7732	Intermediate Similarity	NPC184063
0.7732	Intermediate Similarity	NPC470379
0.7732	Intermediate Similarity	NPC470373
0.7723	Intermediate Similarity	NPC477512
0.7714	Intermediate Similarity	NPC55972
0.7714	Intermediate Similarity	NPC327286
0.7714	Intermediate Similarity	NPC233379
0.7714	Intermediate Similarity	NPC169888

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 NPC190294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	2603
0.2-0.3	3667
0.3-0.4	1682
0.4-0.5	563
0.5-0.6	257
0.6-0.7	63
0.7-0.8	2
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
0.766	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6698	Approved
0.7449	Intermediate Similarity	NPD46	Approved
0.72	Intermediate Similarity	NPD7983	Approved
0.7182	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7838	Discovery
0.7091	Intermediate Similarity	NPD6371	Approved
0.6909	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1695	Approved
0.6757	Remote Similarity	NPD6686	Approved
0.6731	Remote Similarity	NPD5282	Discontinued
0.6695	Remote Similarity	NPD6319	Approved
0.6636	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8297	Approved
0.65	Remote Similarity	NPD8515	Approved
0.65	Remote Similarity	NPD8516	Approved
0.65	Remote Similarity	NPD8517	Approved
0.65	Remote Similarity	NPD8513	Phase 3
0.6481	Remote Similarity	NPD4225	Approved
0.6466	Remote Similarity	NPD4632	Approved
0.6465	Remote Similarity	NPD6435	Approved
0.6435	Remote Similarity	NPD6650	Approved
0.6435	Remote Similarity	NPD6649	Approved
0.6434	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6373	Approved
0.6404	Remote Similarity	NPD6372	Approved
0.6379	Remote Similarity	NPD6053	Discontinued
0.6372	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD6921	Approved
0.6364	Remote Similarity	NPD5344	Discontinued
0.6341	Remote Similarity	NPD7492	Approved
0.6325	Remote Similarity	NPD8133	Approved
0.6321	Remote Similarity	NPD5778	Approved
0.6321	Remote Similarity	NPD5779	Approved
0.6316	Remote Similarity	NPD6881	Approved
0.6316	Remote Similarity	NPD6899	Approved
0.6311	Remote Similarity	NPD8080	Discontinued
0.6303	Remote Similarity	NPD6009	Approved
0.629	Remote Similarity	NPD6616	Approved
0.6286	Remote Similarity	NPD5785	Approved
0.6283	Remote Similarity	NPD5739	Approved
0.6283	Remote Similarity	NPD6675	Approved
0.6283	Remote Similarity	NPD7128	Approved
0.6283	Remote Similarity	NPD6402	Approved
0.6281	Remote Similarity	NPD6054	Approved
0.6263	Remote Similarity	NPD5368	Approved
0.6261	Remote Similarity	NPD6013	Approved
0.6261	Remote Similarity	NPD6014	Approved
0.6261	Remote Similarity	NPD6012	Approved
0.6261	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7642	Approved
0.626	Remote Similarity	NPD8328	Phase 3
0.625	Remote Similarity	NPD7641	Discontinued
0.624	Remote Similarity	NPD8074	Phase 3
0.624	Remote Similarity	NPD7078	Approved
0.6239	Remote Similarity	NPD6882	Approved
0.6238	Remote Similarity	NPD6110	Phase 1
0.6238	Remote Similarity	NPD7154	Phase 3
0.623	Remote Similarity	NPD6016	Approved
0.623	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.623	Remote Similarity	NPD8269	Approved
0.623	Remote Similarity	NPD6015	Approved
0.623	Remote Similarity	NPD8268	Approved
0.623	Remote Similarity	NPD8267	Approved
0.623	Remote Similarity	NPD5983	Phase 2
0.623	Remote Similarity	NPD8266	Approved
0.6228	Remote Similarity	NPD5701	Approved
0.6214	Remote Similarity	NPD4249	Approved
0.6214	Remote Similarity	NPD5786	Approved
0.6207	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6883	Approved
0.6207	Remote Similarity	NPD7290	Approved
0.6207	Remote Similarity	NPD7102	Approved
0.62	Remote Similarity	NPD5369	Approved
0.6195	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7736	Approved
0.6179	Remote Similarity	NPD5988	Approved
0.6179	Remote Similarity	NPD6370	Approved
0.6174	Remote Similarity	NPD7320	Approved
0.6174	Remote Similarity	NPD6011	Approved
0.6172	Remote Similarity	NPD7260	Phase 2
0.6167	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7115	Discovery
0.616	Remote Similarity	NPD7507	Approved
0.6154	Remote Similarity	NPD6869	Approved
0.6154	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD4250	Approved
0.6154	Remote Similarity	NPD4251	Approved
0.6154	Remote Similarity	NPD6847	Approved
0.6154	Remote Similarity	NPD6617	Approved
0.6148	Remote Similarity	NPD6059	Approved
0.6147	Remote Similarity	NPD7839	Suspended
0.6129	Remote Similarity	NPD7604	Phase 2
0.6124	Remote Similarity	NPD6845	Suspended
0.6117	Remote Similarity	NPD5363	Approved
0.6111	Remote Similarity	NPD8293	Discontinued
0.6091	Remote Similarity	NPD6084	Phase 2
0.6091	Remote Similarity	NPD6083	Phase 2
0.6055	Remote Similarity	NPD5695	Phase 3
0.6044	Remote Similarity	NPD7909	Approved
0.6038	Remote Similarity	NPD6101	Approved
0.6038	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5696	Approved
0.6032	Remote Similarity	NPD8451	Approved
0.6032	Remote Similarity	NPD6336	Discontinued
0.6016	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD7830	Approved
0.5984	Remote Similarity	NPD8448	Approved
0.5982	Remote Similarity	NPD6648	Approved
0.598	Remote Similarity	NPD4270	Approved
0.598	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4269	Approved
0.5968	Remote Similarity	NPD8444	Approved
0.5962	Remote Similarity	NPD1694	Approved
0.5962	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6274	Approved
0.5948	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6412	Phase 2
0.5941	Remote Similarity	NPD4819	Approved
0.5941	Remote Similarity	NPD4822	Approved
0.5941	Remote Similarity	NPD4821	Approved
0.5941	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4820	Approved
0.5932	Remote Similarity	NPD4634	Approved
0.5926	Remote Similarity	NPD6411	Approved
0.5922	Remote Similarity	NPD5362	Discontinued
0.5902	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7638	Approved
0.5882	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2204	Approved
0.5877	Remote Similarity	NPD5211	Phase 2
0.5872	Remote Similarity	NPD6399	Phase 3
0.5865	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD8391	Approved
0.5846	Remote Similarity	NPD8390	Approved
0.5846	Remote Similarity	NPD8392	Approved
0.5841	Remote Similarity	NPD7640	Approved
0.5841	Remote Similarity	NPD4696	Approved
0.5841	Remote Similarity	NPD5286	Approved
0.5841	Remote Similarity	NPD7639	Approved
0.5841	Remote Similarity	NPD5285	Approved
0.5827	Remote Similarity	NPD8342	Approved
0.5827	Remote Similarity	NPD8340	Approved
0.5827	Remote Similarity	NPD8299	Approved
0.5827	Remote Similarity	NPD8341	Approved
0.5825	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7101	Approved
0.5806	Remote Similarity	NPD7100	Approved
0.5804	Remote Similarity	NPD4755	Approved
0.58	Remote Similarity	NPD4756	Discovery
0.5789	Remote Similarity	NPD8415	Approved
0.5789	Remote Similarity	NPD1700	Approved
0.5784	Remote Similarity	NPD4252	Approved
0.5781	Remote Similarity	NPD8273	Phase 1
0.578	Remote Similarity	NPD5693	Phase 1
0.5776	Remote Similarity	NPD5141	Approved
0.5772	Remote Similarity	NPD6317	Approved
0.5743	Remote Similarity	NPD4268	Approved
0.5743	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4271	Approved
0.5739	Remote Similarity	NPD8085	Approved
0.5739	Remote Similarity	NPD8083	Approved
0.5739	Remote Similarity	NPD8138	Approved
0.5739	Remote Similarity	NPD4633	Approved
0.5739	Remote Similarity	NPD5226	Approved
0.5739	Remote Similarity	NPD8086	Approved
0.5739	Remote Similarity	NPD8084	Approved
0.5739	Remote Similarity	NPD8082	Approved
0.5739	Remote Similarity	NPD5225	Approved
0.5739	Remote Similarity	NPD5224	Approved
0.5739	Remote Similarity	NPD8139	Approved
0.5726	Remote Similarity	NPD6313	Approved
0.5726	Remote Similarity	NPD6314	Approved
0.5726	Remote Similarity	NPD6335	Approved
0.5714	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD4700	Approved
0.5699	Remote Similarity	NPD3197	Phase 1
0.5692	Remote Similarity	NPD6033	Approved
0.569	Remote Similarity	NPD8276	Approved
0.569	Remote Similarity	NPD5175	Approved
0.569	Remote Similarity	NPD8275	Approved
0.569	Remote Similarity	NPD5174	Approved
0.5652	Remote Similarity	NPD5223	Approved
0.5648	Remote Similarity	NPD5737	Approved
0.5648	Remote Similarity	NPD6672	Approved
0.5641	Remote Similarity	NPD8081	Approved
0.5638	Remote Similarity	NPD7341	Phase 2
0.5636	Remote Similarity	NPD8035	Phase 2
0.5636	Remote Similarity	NPD8034	Phase 2
0.563	Remote Similarity	NPD4729	Approved
0.563	Remote Similarity	NPD4730	Approved
0.5625	Remote Similarity	NPD4629	Approved
0.5625	Remote Similarity	NPD5210	Approved
0.5618	Remote Similarity	NPD73	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