NPASS Compound

Structure

NPC471142 OpenBabel07101719132D 32 33 0 0 1 0 0 0 0 0999 V2000 -1.7987 -4.7786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8915 -3.5650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7886 -2.3088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3649 -5.1537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4629 -4.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2714 -0.2134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5172 0.1595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4589 -1.9970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6509 1.1803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9947 -3.8563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3172 -1.4922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1689 -4.2314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4549 0.2580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6549 -1.0748 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7582 -2.6279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8165 -0.4714 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6205 -1.3937 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8205 -2.7265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0040 -2.2550 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2941 -3.2255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7007 -0.6309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1417 -3.4892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9503 1.8112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8696 -3.6005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5926 -0.9762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4901 -2.3032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6229 -0.4349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5875 -4.2520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0794 -3.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6245 -3.6487 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 -0.3974 -3.5168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 2 0 0 0 0 4 12 1 0 0 0 0 5 29 1 0 0 0 0 6 13 1 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 8 15 2 0 0 0 0 9 13 1 0 0 0 0 9 23 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 24 2 0 0 0 0 12 30 1 0 0 0 0 14 25 1 6 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 16 7 1 6 0 0 0 16 17 1 0 0 0 0 16 31 1 0 0 0 0 17 11 1 1 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 18 30 1 1 0 0 0 19 32 1 1 0 0 0 20 26 2 0 0 0 0 20 32 1 0 0 0 0 21 27 2 0 0 0 0 21 31 1 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.17
Volume:	441.402
LogP:	0.78
LogD:	0.39
LogS:	-2.225
# Rotatable Bonds:	8
TPSA:	139.34
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.256
Synthetic Accessibility Score:	5.086
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.858
MDCK Permeability:	8.30592107377015e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.588
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.425
Plasma Protein Binding (PPB):	55.26615524291992%
Volume Distribution (VD):	0.507
Pgp-substrate:	61.39053726196289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.491
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.422
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	7.101
Half-life (T1/2):	0.81

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.818
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.714
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.815
Carcinogencity:	0.046
Eye Corrosion:	0.035
Eye Irritation:	0.028
Respiratory Toxicity:	0.298

Download Data

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

Natural Product: NPC471142

Natural Product ID:	NPC471142
*Common Name:**	Melcanthin C
IUPAC Name:	methyl (3aS,4S,5R,6E,8S,10E,11aR)-5-acetyloxy-8-hydroxy-10-(hydroxymethyl)-3-methylidene-4-(2-methylpropanoyloxy)-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate
Synonyms:
Standard InCHIKey:	ITNBCDHJIVJLJO-OQESSQTCSA-N
Standard InCHI:	InChI=1S/C22H28O10/c1-10(2)20(26)32-19-17-11(3)21(27)31-16(17)7-13(9-23)6-14(25)8-15(22(28)29-5)18(19)30-12(4)24/h7-8,10,14,16-19,23,25H,3,6,9H2,1-2,4-5H3/b13-7+,15-8+/t14-,16+,17-,18+,19-/m0/s1
SMILES:	CC(C)C(=O)OC1C2C(C=C(CC(C=C(C1OC(=O)C)C(=O)OC)O)CO)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380781
PubChem CID:	73354912
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
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	San Antonio, Texas	2004-JUN	PMID[25685941]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	n.a.	n.a.	PMID[25685941]
NPO18602	Melampodium leucanthum	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	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	4677.35	nM	PMID[464100]
NPT27	Others	Unspecified		IC50	=	24820.0	nM	PMID[464100]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	4680.0	nM	PMID[464100]

☑ 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 NPC471142 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	202
0.1-0.2	1364
0.2-0.3	4787
0.3-0.4	8384
0.4-0.5	15021
0.5-0.6	7660
0.6-0.7	3903
0.7-0.8	1108
0.8-0.85	160
0.85-0.9	80
0.9-0.95	25
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC477922
0.9457	High Similarity	NPC471144
0.9451	High Similarity	NPC477921
0.9438	High Similarity	NPC473321
0.9355	High Similarity	NPC288876
0.9326	High Similarity	NPC473619
0.9121	High Similarity	NPC162205
0.9121	High Similarity	NPC295204
0.9121	High Similarity	NPC273579
0.9121	High Similarity	NPC288240
0.9111	High Similarity	NPC474232
0.9101	High Similarity	NPC475819
0.9101	High Similarity	NPC473715
0.9032	High Similarity	NPC279621
0.9032	High Similarity	NPC473859
0.9032	High Similarity	NPC230800
0.9	High Similarity	NPC474032
0.8977	High Similarity	NPC470755
0.8958	High Similarity	NPC149371
0.8947	High Similarity	NPC475949
0.8925	High Similarity	NPC475659
0.8925	High Similarity	NPC36954
0.8913	High Similarity	NPC475912
0.8901	High Similarity	NPC475855
0.8889	High Similarity	NPC476805
0.8876	High Similarity	NPC469910
0.8864	High Similarity	NPC158756
0.8854	High Similarity	NPC47880
0.883	High Similarity	NPC476315
0.883	High Similarity	NPC17585
0.8817	High Similarity	NPC303942
0.8817	High Similarity	NPC474247
0.8817	High Similarity	NPC57405
0.8788	High Similarity	NPC477513
0.8764	High Similarity	NPC21469
0.875	High Similarity	NPC473390
0.875	High Similarity	NPC116543
0.875	High Similarity	NPC169575
0.875	High Similarity	NPC40746
0.875	High Similarity	NPC131669
0.8723	High Similarity	NPC14961
0.8723	High Similarity	NPC270013
0.871	High Similarity	NPC125674
0.871	High Similarity	NPC475838
0.871	High Similarity	NPC476300
0.871	High Similarity	NPC228451
0.8696	High Similarity	NPC179394
0.8696	High Similarity	NPC144133
0.8681	High Similarity	NPC476803
0.8667	High Similarity	NPC475461
0.8667	High Similarity	NPC305475
0.8646	High Similarity	NPC473326
0.8636	High Similarity	NPC229825
0.8617	High Similarity	NPC81386
0.8617	High Similarity	NPC474035
0.8602	High Similarity	NPC30515
0.8602	High Similarity	NPC184463
0.8587	High Similarity	NPC295312
0.8586	High Similarity	NPC100487
0.8557	High Similarity	NPC477512
0.8556	High Similarity	NPC255307
0.8542	High Similarity	NPC40812
0.8526	High Similarity	NPC471141
0.8523	High Similarity	NPC24417
0.8511	High Similarity	NPC212486
0.8511	High Similarity	NPC81419
0.8511	High Similarity	NPC179746
0.8495	Intermediate Similarity	NPC476004
0.8495	Intermediate Similarity	NPC51004
0.8495	Intermediate Similarity	NPC474761
0.8485	Intermediate Similarity	NPC472755
0.8485	Intermediate Similarity	NPC475871
0.8485	Intermediate Similarity	NPC475945
0.8478	Intermediate Similarity	NPC202672
0.8469	Intermediate Similarity	NPC264477
0.8469	Intermediate Similarity	NPC164598
0.8469	Intermediate Similarity	NPC474339
0.8469	Intermediate Similarity	NPC201718
0.8469	Intermediate Similarity	NPC477511
0.8454	Intermediate Similarity	NPC474213
0.8454	Intermediate Similarity	NPC255592
0.8454	Intermediate Similarity	NPC261377
0.8454	Intermediate Similarity	NPC308567
0.8444	Intermediate Similarity	NPC476804
0.8444	Intermediate Similarity	NPC114979
0.8444	Intermediate Similarity	NPC191476
0.8438	Intermediate Similarity	NPC306041
0.8421	Intermediate Similarity	NPC473316
0.8421	Intermediate Similarity	NPC471147
0.8421	Intermediate Similarity	NPC140543
0.8421	Intermediate Similarity	NPC473330
0.8404	Intermediate Similarity	NPC208886
0.8404	Intermediate Similarity	NPC12172
0.84	Intermediate Similarity	NPC203659
0.8387	Intermediate Similarity	NPC166919
0.8387	Intermediate Similarity	NPC307411
0.8387	Intermediate Similarity	NPC151770
0.8384	Intermediate Similarity	NPC471148
0.8384	Intermediate Similarity	NPC474747
0.8351	Intermediate Similarity	NPC471462
0.8333	Intermediate Similarity	NPC59097
0.8316	Intermediate Similarity	NPC469692
0.8316	Intermediate Similarity	NPC469645
0.8316	Intermediate Similarity	NPC475302
0.83	Intermediate Similarity	NPC110989
0.8298	Intermediate Similarity	NPC71533
0.8298	Intermediate Similarity	NPC106510
0.8298	Intermediate Similarity	NPC475748
0.8295	Intermediate Similarity	NPC98557
0.8295	Intermediate Similarity	NPC167881
0.8283	Intermediate Similarity	NPC110443
0.8283	Intermediate Similarity	NPC128733
0.8283	Intermediate Similarity	NPC185141
0.8283	Intermediate Similarity	NPC133907
0.8283	Intermediate Similarity	NPC474742
0.8283	Intermediate Similarity	NPC46998
0.8265	Intermediate Similarity	NPC187761
0.8265	Intermediate Similarity	NPC83895
0.8265	Intermediate Similarity	NPC208233
0.8265	Intermediate Similarity	NPC187268
0.8261	Intermediate Similarity	NPC150755
0.8261	Intermediate Similarity	NPC469483
0.8247	Intermediate Similarity	NPC39859
0.8247	Intermediate Similarity	NPC76862
0.8247	Intermediate Similarity	NPC470883
0.8247	Intermediate Similarity	NPC158416
0.8247	Intermediate Similarity	NPC35498
0.8242	Intermediate Similarity	NPC96259
0.8242	Intermediate Similarity	NPC141193
0.8229	Intermediate Similarity	NPC476267
0.8229	Intermediate Similarity	NPC121825
0.8218	Intermediate Similarity	NPC220964
0.8218	Intermediate Similarity	NPC477510
0.8218	Intermediate Similarity	NPC475676
0.8218	Intermediate Similarity	NPC471143
0.8218	Intermediate Similarity	NPC474741
0.8211	Intermediate Similarity	NPC158061
0.82	Intermediate Similarity	NPC472754
0.82	Intermediate Similarity	NPC320019
0.82	Intermediate Similarity	NPC324017
0.82	Intermediate Similarity	NPC225353
0.8191	Intermediate Similarity	NPC477011
0.8182	Intermediate Similarity	NPC108816
0.8182	Intermediate Similarity	NPC93763
0.8182	Intermediate Similarity	NPC471465
0.8182	Intermediate Similarity	NPC196653
0.8172	Intermediate Similarity	NPC231889
0.8172	Intermediate Similarity	NPC160138
0.8163	Intermediate Similarity	NPC471140
0.8144	Intermediate Similarity	NPC304886
0.8137	Intermediate Similarity	NPC223450
0.8137	Intermediate Similarity	NPC243998
0.8132	Intermediate Similarity	NPC250315
0.8119	Intermediate Similarity	NPC69171
0.8119	Intermediate Similarity	NPC474165
0.8119	Intermediate Similarity	NPC4620
0.8111	Intermediate Similarity	NPC52861
0.8105	Intermediate Similarity	NPC473455
0.8105	Intermediate Similarity	NPC469368
0.81	Intermediate Similarity	NPC15993
0.81	Intermediate Similarity	NPC476270
0.81	Intermediate Similarity	NPC472753
0.809	Intermediate Similarity	NPC270126
0.8085	Intermediate Similarity	NPC153805
0.8085	Intermediate Similarity	NPC474471
0.8085	Intermediate Similarity	NPC280621
0.8085	Intermediate Similarity	NPC227379
0.8085	Intermediate Similarity	NPC287089
0.8085	Intermediate Similarity	NPC233551
0.8085	Intermediate Similarity	NPC40376
0.8085	Intermediate Similarity	NPC48338
0.8085	Intermediate Similarity	NPC21208
0.8085	Intermediate Similarity	NPC89001
0.8085	Intermediate Similarity	NPC20339
0.8081	Intermediate Similarity	NPC141191
0.8077	Intermediate Similarity	NPC38154
0.8068	Intermediate Similarity	NPC141789
0.8068	Intermediate Similarity	NPC116177
0.8068	Intermediate Similarity	NPC320630
0.8068	Intermediate Similarity	NPC171204
0.8068	Intermediate Similarity	NPC476028
0.8068	Intermediate Similarity	NPC7563
0.8065	Intermediate Similarity	NPC284902
0.8065	Intermediate Similarity	NPC112685
0.8065	Intermediate Similarity	NPC50637
0.8061	Intermediate Similarity	NPC476009
0.8041	Intermediate Similarity	NPC474338
0.8041	Intermediate Similarity	NPC190294
0.8039	Intermediate Similarity	NPC472756
0.8021	Intermediate Similarity	NPC300312
0.8021	Intermediate Similarity	NPC111114
0.8021	Intermediate Similarity	NPC261607
0.802	Intermediate Similarity	NPC86077
0.802	Intermediate Similarity	NPC183571
0.8	Intermediate Similarity	NPC281132
0.8	Intermediate Similarity	NPC14901
0.8	Intermediate Similarity	NPC92974
0.8	Intermediate Similarity	NPC477017
0.8	Intermediate Similarity	NPC280612
0.8	Intermediate Similarity	NPC87306

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 NPC471142 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1983
0.2-0.3	3673
0.3-0.4	2136
0.4-0.5	793
0.5-0.6	288
0.6-0.7	71
0.7-0.8	12
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
0.8021	Intermediate Similarity	NPD7983	Approved
0.7957	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD46	Approved
0.7917	Intermediate Similarity	NPD6698	Approved
0.7885	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD6371	Approved
0.7551	Intermediate Similarity	NPD7838	Discovery
0.7379	Intermediate Similarity	NPD4225	Approved
0.7228	Intermediate Similarity	NPD5778	Approved
0.7228	Intermediate Similarity	NPD5779	Approved
0.7212	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5785	Approved
0.7156	Intermediate Similarity	NPD6686	Approved
0.7117	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5363	Approved
0.7019	Intermediate Similarity	NPD7839	Suspended
0.7009	Intermediate Similarity	NPD8517	Approved
0.7009	Intermediate Similarity	NPD8515	Approved
0.7009	Intermediate Similarity	NPD8516	Approved
0.7009	Intermediate Similarity	NPD8513	Phase 3
0.697	Remote Similarity	NPD4249	Approved
0.697	Remote Similarity	NPD5786	Approved
0.6931	Remote Similarity	NPD1695	Approved
0.69	Remote Similarity	NPD4251	Approved
0.69	Remote Similarity	NPD4250	Approved
0.6837	Remote Similarity	NPD7154	Phase 3
0.6827	Remote Similarity	NPD5282	Discontinued
0.6759	Remote Similarity	NPD5344	Discontinued
0.6754	Remote Similarity	NPD6053	Discontinued
0.6735	Remote Similarity	NPD4270	Approved
0.6735	Remote Similarity	NPD4269	Approved
0.6721	Remote Similarity	NPD8074	Phase 3
0.6701	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6612	Remote Similarity	NPD7830	Approved
0.6612	Remote Similarity	NPD7829	Approved
0.6612	Remote Similarity	NPD7642	Approved
0.6602	Remote Similarity	NPD6101	Approved
0.6602	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6435	Approved
0.6514	Remote Similarity	NPD7639	Approved
0.6514	Remote Similarity	NPD6648	Approved
0.6514	Remote Similarity	NPD7640	Approved
0.6512	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6319	Approved
0.65	Remote Similarity	NPD5362	Discontinued
0.65	Remote Similarity	NPD6110	Phase 1
0.6495	Remote Similarity	NPD4271	Approved
0.6495	Remote Similarity	NPD4268	Approved
0.648	Remote Similarity	NPD7319	Approved
0.6476	Remote Similarity	NPD6411	Approved
0.6465	Remote Similarity	NPD5369	Approved
0.6435	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7638	Approved
0.64	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5209	Approved
0.6373	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD1694	Approved
0.6371	Remote Similarity	NPD7507	Approved
0.6371	Remote Similarity	NPD8451	Approved
0.6364	Remote Similarity	NPD4821	Approved
0.6364	Remote Similarity	NPD4822	Approved
0.6364	Remote Similarity	NPD5368	Approved
0.6364	Remote Similarity	NPD4820	Approved
0.6364	Remote Similarity	NPD4819	Approved
0.6348	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7641	Discontinued
0.6321	Remote Similarity	NPD7637	Suspended
0.632	Remote Similarity	NPD8448	Approved
0.6311	Remote Similarity	NPD8444	Approved
0.6304	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8341	Approved
0.629	Remote Similarity	NPD7492	Approved
0.629	Remote Similarity	NPD8340	Approved
0.629	Remote Similarity	NPD8299	Approved
0.629	Remote Similarity	NPD8342	Approved
0.6286	Remote Similarity	NPD5370	Suspended
0.6261	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7500	Approved
0.625	Remote Similarity	NPD7260	Phase 2
0.624	Remote Similarity	NPD6616	Approved
0.624	Remote Similarity	NPD8273	Phase 1
0.6239	Remote Similarity	NPD2204	Approved
0.623	Remote Similarity	NPD6054	Approved
0.621	Remote Similarity	NPD8328	Phase 3
0.619	Remote Similarity	NPD7078	Approved
0.6186	Remote Similarity	NPD8297	Approved
0.6179	Remote Similarity	NPD6016	Approved
0.6179	Remote Similarity	NPD6015	Approved
0.6174	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD8391	Approved
0.6172	Remote Similarity	NPD8390	Approved
0.6172	Remote Similarity	NPD8392	Approved
0.6168	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6421	Discontinued
0.6142	Remote Similarity	NPD7736	Approved
0.6134	Remote Similarity	NPD4632	Approved
0.6129	Remote Similarity	NPD6370	Approved
0.6129	Remote Similarity	NPD5988	Approved
0.6117	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6649	Approved
0.6102	Remote Similarity	NPD6650	Approved
0.6098	Remote Similarity	NPD6059	Approved
0.6087	Remote Similarity	NPD6008	Approved
0.6077	Remote Similarity	NPD6845	Suspended
0.6068	Remote Similarity	NPD6373	Approved
0.6068	Remote Similarity	NPD6372	Approved
0.6063	Remote Similarity	NPD8293	Discontinued
0.6061	Remote Similarity	NPD4756	Discovery
0.6048	Remote Similarity	NPD8269	Approved
0.6048	Remote Similarity	NPD8267	Approved
0.6048	Remote Similarity	NPD8268	Approved
0.6048	Remote Similarity	NPD8266	Approved
0.6034	Remote Similarity	NPD6412	Phase 2
0.6034	Remote Similarity	NPD5697	Approved
0.6019	Remote Similarity	NPD5332	Approved
0.6019	Remote Similarity	NPD5331	Approved
0.6	Remote Similarity	NPD8080	Discontinued
0.5984	Remote Similarity	NPD6009	Approved
0.5984	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6881	Approved
0.5983	Remote Similarity	NPD6899	Approved
0.598	Remote Similarity	NPD4790	Discontinued
0.5965	Remote Similarity	NPD7632	Discontinued
0.5963	Remote Similarity	NPD6399	Phase 3
0.5948	Remote Similarity	NPD6402	Approved
0.5948	Remote Similarity	NPD6675	Approved
0.5948	Remote Similarity	NPD7128	Approved
0.5948	Remote Similarity	NPD5739	Approved
0.594	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6013	Approved
0.5932	Remote Similarity	NPD6014	Approved
0.5932	Remote Similarity	NPD6012	Approved
0.5922	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.592	Remote Similarity	NPD5983	Phase 2
0.5917	Remote Similarity	NPD6882	Approved
0.5914	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD5701	Approved
0.5882	Remote Similarity	NPD7102	Approved
0.5882	Remote Similarity	NPD7290	Approved
0.5882	Remote Similarity	NPD4634	Approved
0.5882	Remote Similarity	NPD6883	Approved
0.5849	Remote Similarity	NPD6422	Discontinued
0.5847	Remote Similarity	NPD7320	Approved
0.5847	Remote Similarity	NPD6011	Approved
0.5833	Remote Similarity	NPD6847	Approved
0.5833	Remote Similarity	NPD6869	Approved
0.5833	Remote Similarity	NPD6617	Approved
0.5833	Remote Similarity	NPD8130	Phase 1
0.5833	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD7604	Phase 2
0.5826	Remote Similarity	NPD5211	Phase 2
0.5812	Remote Similarity	NPD5048	Discontinued
0.5806	Remote Similarity	NPD7327	Approved
0.5806	Remote Similarity	NPD7328	Approved
0.5794	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6921	Approved
0.5794	Remote Similarity	NPD8033	Approved
0.5794	Remote Similarity	NPD7503	Approved
0.576	Remote Similarity	NPD7516	Approved
0.5752	Remote Similarity	NPD6084	Phase 2
0.5752	Remote Similarity	NPD7902	Approved
0.5752	Remote Similarity	NPD6083	Phase 2
0.5746	Remote Similarity	NPD8415	Approved
0.5738	Remote Similarity	NPD8133	Approved
0.5736	Remote Similarity	NPD6336	Discontinued
0.5726	Remote Similarity	NPD5141	Approved
0.5726	Remote Similarity	NPD7505	Discontinued
0.5714	Remote Similarity	NPD5695	Phase 3
0.5714	Remote Similarity	NPD8377	Approved
0.5714	Remote Similarity	NPD8294	Approved
0.5702	Remote Similarity	NPD5696	Approved
0.57	Remote Similarity	NPD8039	Approved
0.5684	Remote Similarity	NPD7331	Phase 2
0.5669	Remote Similarity	NPD8378	Approved
0.5669	Remote Similarity	NPD8380	Approved
0.5669	Remote Similarity	NPD8296	Approved
0.5669	Remote Similarity	NPD8379	Approved
0.5669	Remote Similarity	NPD8335	Approved
0.5667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD4228	Discovery
0.566	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5286	Approved
0.5652	Remote Similarity	NPD4696	Approved
0.5652	Remote Similarity	NPD5285	Approved
0.5649	Remote Similarity	NPD6033	Approved
0.5648	Remote Similarity	NPD7524	Approved
0.5645	Remote Similarity	NPD6274	Approved
0.5641	Remote Similarity	NPD6647	Phase 2
0.5638	Remote Similarity	NPD3197	Phase 1
0.5625	Remote Similarity	NPD7748	Approved
0.562	Remote Similarity	NPD2067	Discontinued
0.5614	Remote Similarity	NPD4755	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