NPASS Compound

Structure

NPC108475 OpenBabel07101719242D 26 28 0 0 1 0 0 0 0 0999 V2000 -3.4392 -1.2458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2324 -2.9654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9388 0.8177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4060 0.8742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4418 -1.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2046 -0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8465 -1.9265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1392 -1.6877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8394 -2.0459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9924 1.1409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4606 -0.8876 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1747 0.5653 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 -1.2467 -2.7266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3746 1.1651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6977 2.0965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2319 2.5772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6397 -3.6462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2975 2.8966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6979 -0.7162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2538 -2.6072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6978 2.1115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 20 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 25 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 20 1 1 0 0 0 14 6 1 1 0 0 0 14 17 1 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 17 19 1 1 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 20 1 6 0 0 0 20 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	368.366
LogP:	1.666
LogD:	1.297
LogS:	-3.595
# Rotatable Bonds:	4
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	4.644
Fsp3:	0.65
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:	-4.844
MDCK Permeability:	2.202043469878845e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.047
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.658

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	56.33495330810547%
Volume Distribution (VD):	0.598
Pgp-substrate:	49.909976959228516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.433
CYP1A2-substrate:	0.488
CYP2C19-inhibitor:	0.861
CYP2C19-substrate:	0.653
CYP2C9-inhibitor:	0.681
CYP2C9-substrate:	0.165
CYP2D6-inhibitor:	0.116
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.525
CYP3A4-substrate:	0.325

ADMET: Excretion

Clearance (CL):	6.815
Half-life (T1/2):	0.798

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.089
AMES Toxicity:	0.142
Rat Oral Acute Toxicity:	0.736
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.92
Carcinogencity:	0.705
Eye Corrosion:	0.21
Eye Irritation:	0.698
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC108475

Natural Product ID:	NPC108475
*Common Name:**	Hispitolide D
IUPAC Name:	[(3aS,6R,6aR,9aS,9bR)-6a-hydroxy-9a-methyl-3-methylidene-2,9-dioxo-4,5,6,7,8,9b-hexahydro-3aH-azuleno[4,5-b]furan-6-yl]methyl 3-methylbut-2-enoate
Synonyms:	Hispitolide D
Standard InCHIKey:	TYAWIPYSWAZYAE-DZDZPLTMSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-11(2)9-16(22)25-10-13-5-6-14-12(3)18(23)26-17(14)19(4)15(21)7-8-20(13,19)24/h9,13-14,17,24H,3,5-8,10H2,1-2,4H3/t13-,14+,17-,19+,20-/m1/s1
SMILES:	CC(=CC(=O)OC[C@H]1CC[C@@H]2[C@H]([C@]3([C@@]1(O)CCC3=O)C)OC(=O)C2=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225011
PubChem CID:	16215286
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:0002046] Ambrosanolides and secoambrosanolides

*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
NPO33481	parthenium hispitum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17291045]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	98.0	%	PMID[507505]

☑ 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 NPC108475 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	247
0.1-0.2	1550
0.2-0.3	5679
0.3-0.4	11555
0.4-0.5	11972
0.5-0.6	6800
0.6-0.7	3993
0.7-0.8	742
0.8-0.85	105
0.85-0.9	37
0.9-0.95	9
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC213947
1.0	High Similarity	NPC170143
0.9556	High Similarity	NPC473273
0.9556	High Similarity	NPC60386
0.9556	High Similarity	NPC308656
0.9556	High Similarity	NPC473234
0.9556	High Similarity	NPC473263
0.9468	High Similarity	NPC171759
0.913	High Similarity	NPC153590
0.9043	High Similarity	NPC18019
0.9043	High Similarity	NPC24956
0.9043	High Similarity	NPC142529
0.9043	High Similarity	NPC91771
0.9043	High Similarity	NPC126156
0.9	High Similarity	NPC201658
0.8925	High Similarity	NPC200237
0.8817	High Similarity	NPC286341
0.8817	High Similarity	NPC191339
0.875	High Similarity	NPC311904
0.871	High Similarity	NPC297474
0.871	High Similarity	NPC54065
0.8632	High Similarity	NPC167219
0.8632	High Similarity	NPC477131
0.8632	High Similarity	NPC473331
0.8617	High Similarity	NPC57304
0.8617	High Similarity	NPC475925
0.8617	High Similarity	NPC35959
0.8617	High Similarity	NPC29821
0.8617	High Similarity	NPC171360
0.8617	High Similarity	NPC184063
0.8617	High Similarity	NPC293001
0.8617	High Similarity	NPC133888
0.8617	High Similarity	NPC63193
0.8602	High Similarity	NPC155935
0.8602	High Similarity	NPC168679
0.8602	High Similarity	NPC12872
0.86	High Similarity	NPC203659
0.8587	High Similarity	NPC118601
0.8557	High Similarity	NPC477949
0.8542	High Similarity	NPC163228
0.8542	High Similarity	NPC67584
0.8526	High Similarity	NPC135776
0.8511	High Similarity	NPC19087
0.8511	High Similarity	NPC35809
0.85	High Similarity	NPC110989
0.8495	Intermediate Similarity	NPC79549
0.8495	Intermediate Similarity	NPC178875
0.8485	Intermediate Similarity	NPC474742
0.8485	Intermediate Similarity	NPC477950
0.8478	Intermediate Similarity	NPC64153
0.8478	Intermediate Similarity	NPC56593
0.8478	Intermediate Similarity	NPC238593
0.8469	Intermediate Similarity	NPC141191
0.8454	Intermediate Similarity	NPC213078
0.8438	Intermediate Similarity	NPC127019
0.8421	Intermediate Similarity	NPC133698
0.8416	Intermediate Similarity	NPC100487
0.8404	Intermediate Similarity	NPC38392
0.8404	Intermediate Similarity	NPC215556
0.84	Intermediate Similarity	NPC225353
0.8387	Intermediate Similarity	NPC24728
0.8384	Intermediate Similarity	NPC280963
0.837	Intermediate Similarity	NPC204105
0.837	Intermediate Similarity	NPC284534
0.837	Intermediate Similarity	NPC300082
0.8367	Intermediate Similarity	NPC169205
0.8367	Intermediate Similarity	NPC161493
0.8351	Intermediate Similarity	NPC48803
0.8351	Intermediate Similarity	NPC90121
0.8351	Intermediate Similarity	NPC275960
0.8351	Intermediate Similarity	NPC52044
0.8351	Intermediate Similarity	NPC193645
0.8351	Intermediate Similarity	NPC304886
0.8351	Intermediate Similarity	NPC213698
0.8351	Intermediate Similarity	NPC476053
0.8333	Intermediate Similarity	NPC54737
0.8317	Intermediate Similarity	NPC475871
0.8317	Intermediate Similarity	NPC475945
0.8316	Intermediate Similarity	NPC301969
0.8316	Intermediate Similarity	NPC37607
0.8316	Intermediate Similarity	NPC216284
0.83	Intermediate Similarity	NPC150923
0.83	Intermediate Similarity	NPC475099
0.8298	Intermediate Similarity	NPC217983
0.8298	Intermediate Similarity	NPC207114
0.8298	Intermediate Similarity	NPC471149
0.828	Intermediate Similarity	NPC304558
0.828	Intermediate Similarity	NPC67493
0.8265	Intermediate Similarity	NPC185553
0.8252	Intermediate Similarity	NPC26617
0.8247	Intermediate Similarity	NPC262133
0.8247	Intermediate Similarity	NPC470010
0.8247	Intermediate Similarity	NPC323008
0.8247	Intermediate Similarity	NPC470013
0.8247	Intermediate Similarity	NPC198853
0.8235	Intermediate Similarity	NPC474741
0.8229	Intermediate Similarity	NPC131209
0.8229	Intermediate Similarity	NPC111114
0.8229	Intermediate Similarity	NPC472705
0.8229	Intermediate Similarity	NPC284185
0.8229	Intermediate Similarity	NPC300312
0.8229	Intermediate Similarity	NPC70595
0.8229	Intermediate Similarity	NPC155215
0.8229	Intermediate Similarity	NPC150978
0.8229	Intermediate Similarity	NPC123177
0.8229	Intermediate Similarity	NPC74103
0.8229	Intermediate Similarity	NPC261607
0.8222	Intermediate Similarity	NPC6823
0.8218	Intermediate Similarity	NPC474747
0.8211	Intermediate Similarity	NPC283409
0.8211	Intermediate Similarity	NPC32922
0.819	Intermediate Similarity	NPC477103
0.8182	Intermediate Similarity	NPC471150
0.8182	Intermediate Similarity	NPC474313
0.8172	Intermediate Similarity	NPC235792
0.8163	Intermediate Similarity	NPC170120
0.8163	Intermediate Similarity	NPC475900
0.8163	Intermediate Similarity	NPC472873
0.8155	Intermediate Similarity	NPC243998
0.8155	Intermediate Similarity	NPC223450
0.8152	Intermediate Similarity	NPC245665
0.8152	Intermediate Similarity	NPC54468
0.8144	Intermediate Similarity	NPC258216
0.8137	Intermediate Similarity	NPC475873
0.8125	Intermediate Similarity	NPC253144
0.8125	Intermediate Similarity	NPC71533
0.8125	Intermediate Similarity	NPC106510
0.8119	Intermediate Similarity	NPC116139
0.8105	Intermediate Similarity	NPC91248
0.81	Intermediate Similarity	NPC221615
0.8095	Intermediate Similarity	NPC477102
0.8095	Intermediate Similarity	NPC59489
0.8095	Intermediate Similarity	NPC139838
0.8085	Intermediate Similarity	NPC309757
0.8085	Intermediate Similarity	NPC236692
0.8085	Intermediate Similarity	NPC187661
0.8081	Intermediate Similarity	NPC476009
0.8065	Intermediate Similarity	NPC156485
0.8058	Intermediate Similarity	NPC309190
0.8043	Intermediate Similarity	NPC246076
0.8041	Intermediate Similarity	NPC221282
0.8039	Intermediate Similarity	NPC66110
0.8039	Intermediate Similarity	NPC86077
0.8022	Intermediate Similarity	NPC293418
0.8022	Intermediate Similarity	NPC290508
0.8022	Intermediate Similarity	NPC73052
0.8021	Intermediate Similarity	NPC295312
0.8021	Intermediate Similarity	NPC472872
0.802	Intermediate Similarity	NPC186861
0.8019	Intermediate Similarity	NPC257240
0.8	Intermediate Similarity	NPC190753
0.8	Intermediate Similarity	NPC160138
0.8	Intermediate Similarity	NPC475372
0.798	Intermediate Similarity	NPC469873
0.7979	Intermediate Similarity	NPC21471
0.7979	Intermediate Similarity	NPC33570
0.7963	Intermediate Similarity	NPC209058
0.7957	Intermediate Similarity	NPC215294
0.7957	Intermediate Similarity	NPC318468
0.7941	Intermediate Similarity	NPC201718
0.7941	Intermediate Similarity	NPC206079
0.7941	Intermediate Similarity	NPC62670
0.7938	Intermediate Similarity	NPC179394
0.7938	Intermediate Similarity	NPC62815
0.7938	Intermediate Similarity	NPC129419
0.7938	Intermediate Similarity	NPC144133
0.7935	Intermediate Similarity	NPC47635
0.7928	Intermediate Similarity	NPC312536
0.7921	Intermediate Similarity	NPC244411
0.7921	Intermediate Similarity	NPC54843
0.7909	Intermediate Similarity	NPC473656
0.79	Intermediate Similarity	NPC230800
0.7895	Intermediate Similarity	NPC284902
0.7895	Intermediate Similarity	NPC470242
0.7895	Intermediate Similarity	NPC261253
0.7895	Intermediate Similarity	NPC474045
0.7895	Intermediate Similarity	NPC107787
0.7879	Intermediate Similarity	NPC476267
0.7879	Intermediate Similarity	NPC140543
0.7879	Intermediate Similarity	NPC474338
0.7879	Intermediate Similarity	NPC90453
0.7872	Intermediate Similarity	NPC224386
0.7872	Intermediate Similarity	NPC194859
0.787	Intermediate Similarity	NPC123855
0.787	Intermediate Similarity	NPC76550
0.7864	Intermediate Similarity	NPC149371
0.7857	Intermediate Similarity	NPC290651
0.785	Intermediate Similarity	NPC471884
0.7843	Intermediate Similarity	NPC288876
0.7843	Intermediate Similarity	NPC471381
0.7835	Intermediate Similarity	NPC268298
0.7835	Intermediate Similarity	NPC52198
0.7835	Intermediate Similarity	NPC117405
0.7826	Intermediate Similarity	NPC258965
0.7826	Intermediate Similarity	NPC156658
0.7822	Intermediate Similarity	NPC47834
0.7822	Intermediate Similarity	NPC471462
0.7812	Intermediate Similarity	NPC270270
0.7812	Intermediate Similarity	NPC475703
0.781	Intermediate Similarity	NPC179891

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 NPC108475 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	2255
0.2-0.3	3817
0.3-0.4	1939
0.4-0.5	513
0.5-0.6	265
0.6-0.7	94
0.7-0.8	6
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8351	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD6371	Approved
0.7938	Intermediate Similarity	NPD5785	Approved
0.7653	Intermediate Similarity	NPD1695	Approved
0.7525	Intermediate Similarity	NPD5282	Discontinued
0.7423	Intermediate Similarity	NPD5363	Approved
0.7232	Intermediate Similarity	NPD6053	Discontinued
0.7188	Intermediate Similarity	NPD5369	Approved
0.7172	Intermediate Similarity	NPD5786	Approved
0.7113	Intermediate Similarity	NPD4269	Approved
0.7113	Intermediate Similarity	NPD4270	Approved
0.7075	Intermediate Similarity	NPD4225	Approved
0.7071	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4249	Approved
0.7	Intermediate Similarity	NPD6008	Approved
0.6983	Remote Similarity	NPD7115	Discovery
0.6939	Remote Similarity	NPD5209	Approved
0.6931	Remote Similarity	NPD4251	Approved
0.6931	Remote Similarity	NPD4250	Approved
0.6916	Remote Similarity	NPD7638	Approved
0.6907	Remote Similarity	NPD4252	Approved
0.69	Remote Similarity	NPD1694	Approved
0.6893	Remote Similarity	NPD6698	Approved
0.6893	Remote Similarity	NPD46	Approved
0.6869	Remote Similarity	NPD5362	Discontinued
0.6852	Remote Similarity	NPD7639	Approved
0.6852	Remote Similarity	NPD7640	Approved
0.6792	Remote Similarity	NPD5695	Phase 3
0.6768	Remote Similarity	NPD6435	Approved
0.6768	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD5778	Approved
0.6759	Remote Similarity	NPD5696	Approved
0.6733	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6686	Approved
0.6721	Remote Similarity	NPD7492	Approved
0.6701	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD6054	Approved
0.664	Remote Similarity	NPD7319	Approved
0.6637	Remote Similarity	NPD5697	Approved
0.6613	Remote Similarity	NPD7078	Approved
0.6612	Remote Similarity	NPD6015	Approved
0.6612	Remote Similarity	NPD6016	Approved
0.6604	Remote Similarity	NPD6399	Phase 3
0.6579	Remote Similarity	NPD6899	Approved
0.6579	Remote Similarity	NPD6881	Approved
0.6579	Remote Similarity	NPD7320	Approved
0.6571	Remote Similarity	NPD7838	Discovery
0.6566	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4819	Approved
0.6566	Remote Similarity	NPD4821	Approved
0.6566	Remote Similarity	NPD4820	Approved
0.6566	Remote Similarity	NPD4822	Approved
0.6566	Remote Similarity	NPD5368	Approved
0.656	Remote Similarity	NPD7736	Approved
0.6557	Remote Similarity	NPD6370	Approved
0.6557	Remote Similarity	NPD5988	Approved
0.6552	Remote Similarity	NPD6649	Approved
0.6552	Remote Similarity	NPD6650	Approved
0.6549	Remote Similarity	NPD5739	Approved
0.6549	Remote Similarity	NPD6675	Approved
0.6549	Remote Similarity	NPD6402	Approved
0.6549	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD6903	Approved
0.6535	Remote Similarity	NPD7154	Phase 3
0.6532	Remote Similarity	NPD7507	Approved
0.6529	Remote Similarity	NPD6059	Approved
0.6522	Remote Similarity	NPD6012	Approved
0.6522	Remote Similarity	NPD6373	Approved
0.6522	Remote Similarity	NPD6013	Approved
0.6522	Remote Similarity	NPD6372	Approved
0.6522	Remote Similarity	NPD6014	Approved
0.6509	Remote Similarity	NPD6411	Approved
0.6509	Remote Similarity	NPD5693	Phase 1
0.6505	Remote Similarity	NPD7146	Approved
0.6505	Remote Similarity	NPD7334	Approved
0.6505	Remote Similarity	NPD6409	Approved
0.6505	Remote Similarity	NPD5330	Approved
0.6505	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7521	Approved
0.6505	Remote Similarity	NPD6684	Approved
0.6491	Remote Similarity	NPD5701	Approved
0.6481	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8293	Discontinued
0.6466	Remote Similarity	NPD6883	Approved
0.6466	Remote Similarity	NPD7290	Approved
0.6466	Remote Similarity	NPD7102	Approved
0.6441	Remote Similarity	NPD4632	Approved
0.6435	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6011	Approved
0.6415	Remote Similarity	NPD5207	Approved
0.641	Remote Similarity	NPD8130	Phase 1
0.641	Remote Similarity	NPD6869	Approved
0.641	Remote Similarity	NPD6617	Approved
0.641	Remote Similarity	NPD6847	Approved
0.6381	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5331	Approved
0.6373	Remote Similarity	NPD5332	Approved
0.6364	Remote Similarity	NPD4268	Approved
0.6364	Remote Similarity	NPD4271	Approved
0.6356	Remote Similarity	NPD8297	Approved
0.6356	Remote Similarity	NPD6882	Approved
0.6355	Remote Similarity	NPD5281	Approved
0.6355	Remote Similarity	NPD5284	Approved
0.6348	Remote Similarity	NPD6412	Phase 2
0.6337	Remote Similarity	NPD4790	Discontinued
0.633	Remote Similarity	NPD5210	Approved
0.633	Remote Similarity	NPD4629	Approved
0.6325	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4634	Approved
0.6321	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6101	Approved
0.6321	Remote Similarity	NPD4753	Phase 2
0.6311	Remote Similarity	NPD3666	Approved
0.6311	Remote Similarity	NPD3665	Phase 1
0.6311	Remote Similarity	NPD3133	Approved
0.6306	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7632	Discontinued
0.6283	Remote Similarity	NPD5211	Phase 2
0.6281	Remote Similarity	NPD6009	Approved
0.6279	Remote Similarity	NPD7260	Phase 2
0.6273	Remote Similarity	NPD7839	Suspended
0.6271	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD5286	Approved
0.6239	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6001	Approved
0.6231	Remote Similarity	NPD6845	Suspended
0.6226	Remote Similarity	NPD5737	Approved
0.6226	Remote Similarity	NPD6672	Approved
0.6216	Remote Similarity	NPD4755	Approved
0.621	Remote Similarity	NPD8516	Approved
0.621	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.621	Remote Similarity	NPD8515	Approved
0.621	Remote Similarity	NPD8513	Phase 3
0.621	Remote Similarity	NPD5983	Phase 2
0.621	Remote Similarity	NPD8517	Approved
0.62	Remote Similarity	NPD4802	Phase 2
0.62	Remote Similarity	NPD4238	Approved
0.6198	Remote Similarity	NPD6274	Approved
0.6195	Remote Similarity	NPD5344	Discontinued
0.619	Remote Similarity	NPD3618	Phase 1
0.6174	Remote Similarity	NPD5141	Approved
0.6168	Remote Similarity	NPD6080	Approved
0.6168	Remote Similarity	NPD6673	Approved
0.6168	Remote Similarity	NPD5370	Suspended
0.6168	Remote Similarity	NPD6904	Approved
0.614	Remote Similarity	NPD5224	Approved
0.614	Remote Similarity	NPD5225	Approved
0.614	Remote Similarity	NPD4633	Approved
0.614	Remote Similarity	NPD5226	Approved
0.6134	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4221	Approved
0.6117	Remote Similarity	NPD4223	Phase 3
0.6117	Remote Similarity	NPD3667	Approved
0.6111	Remote Similarity	NPD7604	Phase 2
0.6111	Remote Similarity	NPD5692	Phase 3
0.6106	Remote Similarity	NPD6648	Approved
0.6106	Remote Similarity	NPD4700	Approved
0.6098	Remote Similarity	NPD7328	Approved
0.6098	Remote Similarity	NPD7327	Approved
0.6091	Remote Similarity	NPD7748	Approved
0.6087	Remote Similarity	NPD5175	Approved
0.6087	Remote Similarity	NPD5174	Approved
0.608	Remote Similarity	NPD8033	Approved
0.6077	Remote Similarity	NPD5956	Approved
0.6075	Remote Similarity	NPD5208	Approved
0.6071	Remote Similarity	NPD7902	Approved
0.6068	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4788	Approved
0.6058	Remote Similarity	NPD6695	Phase 3
0.6055	Remote Similarity	NPD6079	Approved
0.6055	Remote Similarity	NPD8035	Phase 2
0.6055	Remote Similarity	NPD5694	Approved
0.6055	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD8034	Phase 2
0.6055	Remote Similarity	NPD6050	Approved
0.6053	Remote Similarity	NPD5223	Approved
0.6048	Remote Similarity	NPD7516	Approved
0.6048	Remote Similarity	NPD7101	Approved
0.6048	Remote Similarity	NPD7100	Approved
0.6047	Remote Similarity	NPD6033	Approved
0.6038	Remote Similarity	NPD5690	Phase 2
0.6038	Remote Similarity	NPD5279	Phase 3
0.6019	Remote Similarity	NPD5328	Approved
0.6019	Remote Similarity	NPD6051	Approved
0.6016	Remote Similarity	NPD6317	Approved
0.6016	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD8294	Approved
0.6	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4202	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