NPASS Compound

Structure

NPC474741 OpenBabel07101719242D 27 29 0 0 1 0 0 0 0 0999 V2000 -2.1133 -3.8525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9368 -1.6773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0632 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4620 2.5460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1962 -0.4477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0442 -3.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4368 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1932 -2.4983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4368 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4769 1.5461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2406 -0.1530 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4114 -1.8748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2946 0.9705 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0915 0.8359 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2255 1.3359 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9999 0.0150 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5632 -0.8113 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0632 -1.6773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3232 0.9463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5604 -0.8860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4805 -2.2402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4368 -0.8113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2788 1.2411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3422 -1.5095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0915 1.8359 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 -1.0632 -1.6773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 7 9 2 0 0 0 0 8 12 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 1 0 0 0 12 20 1 0 0 0 0 12 21 2 0 0 0 0 13 10 1 6 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 6 0 0 0 15 25 1 6 0 0 0 16 17 1 0 0 0 0 16 26 1 1 0 0 0 17 20 1 6 0 0 0 17 27 1 0 0 0 0 18 22 2 0 0 0 0 18 27 1 0 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 20 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.15
Volume:	374.52
LogP:	1.647
LogD:	1.252
LogS:	-3.228
# Rotatable Bonds:	5
TPSA:	102.43
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	5.151
Fsp3:	0.55
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:	-4.745
MDCK Permeability:	3.431615550653078e-05
Pgp-inhibitor:	0.325
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.131
20% Bioavailability (F20%):	0.912
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.645
Plasma Protein Binding (PPB):	54.34165573120117%
Volume Distribution (VD):	1.711
Pgp-substrate:	34.9851188659668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.443
CYP1A2-substrate:	0.622
CYP2C19-inhibitor:	0.344
CYP2C19-substrate:	0.683
CYP2C9-inhibitor:	0.236
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.183
CYP3A4-substrate:	0.275

ADMET: Excretion

Clearance (CL):	8.246
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.893
Drug-inuced Liver Injury (DILI):	0.746
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.858
Maximum Recommended Daily Dose:	0.338
Skin Sensitization:	0.639
Carcinogencity:	0.457
Eye Corrosion:	0.573
Eye Irritation:	0.108
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC474741

Natural Product ID:	NPC474741
*Common Name:**	(1S,5S,6R,7R,8R,9S,10S)-5-Angeloyloxy-8,9-Epoxy-1-Hydroxy-2-Oxaxantha-3,11-Dien-6,12-Olide
IUPAC Name:	[(1aS,2S,3S,4S,4aR,7aS,7bR)-3-[(E)-but-2-enoyl]-3-hydroxy-2-methyl-7-methylidene-6-oxo-1a,2,4,4a,7a,7b-hexahydrooxireno[3,4]cyclohepta[1,3-b]furan-4-yl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	BHTATZDUYXWHPP-AGLMJVFUSA-N
Standard InCHI:	InChI=1S/C20H24O7/c1-6-8-12(21)20(24)11(5)14-15(25-14)13-10(4)19(23)26-16(13)17(20)27-18(22)9(3)7-2/h6-8,11,13-17,24H,4H2,1-3,5H3/b8-6+,9-7-/t11-,13-,14-,15+,16+,17-,20+/m0/s1
SMILES:	C/C=C/C(=O)[C@@]1(O)[C@@H](OC(=O)/C(=CC)/C)[C@@H]2OC(=O)C(=C)[C@H]2[C@@H]2[C@H]([C@@H]1C)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481063
PubChem CID:	44575367
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO21597	Ratibida columnifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579870]
NPO21597	Ratibida columnifera	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
ED50	8

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2049	Cell Line	HT	Homo sapiens	ED50	=	0.16	ug ml-1	PMID[476614]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	0.5	ug ml-1	PMID[476614]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[476614]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[476614]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.3	ug ml-1	PMID[476614]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.9	ug ml-1	PMID[476614]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.2	ug ml-1	PMID[476614]

☑ 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 NPC474741 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	246
0.1-0.2	1407
0.2-0.3	4822
0.3-0.4	8774
0.4-0.5	14696
0.5-0.6	7658
0.6-0.7	3609
0.7-0.8	1224
0.8-0.85	211
0.85-0.9	41
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9691	High Similarity	NPC475945
0.9691	High Similarity	NPC475871
0.9688	High Similarity	NPC474742
0.9588	High Similarity	NPC474747
0.9293	High Similarity	NPC475873
0.9192	High Similarity	NPC149371
0.9091	High Similarity	NPC474339
0.9091	High Similarity	NPC47880
0.9091	High Similarity	NPC164598
0.901	High Similarity	NPC203659
0.8972	High Similarity	NPC471146
0.8969	High Similarity	NPC475900
0.8911	High Similarity	NPC110989
0.89	High Similarity	NPC201718
0.89	High Similarity	NPC476270
0.8878	High Similarity	NPC476009
0.8835	High Similarity	NPC477513
0.8812	High Similarity	NPC225353
0.88	High Similarity	NPC288876
0.8776	High Similarity	NPC270013
0.8776	High Similarity	NPC475659
0.8776	High Similarity	NPC14961
0.8763	High Similarity	NPC212486
0.875	High Similarity	NPC62815
0.8738	High Similarity	NPC243998
0.8738	High Similarity	NPC223450
0.8713	High Similarity	NPC472753
0.87	High Similarity	NPC471144
0.8687	High Similarity	NPC473859
0.8673	High Similarity	NPC81386
0.8673	High Similarity	NPC474035
0.866	High Similarity	NPC20713
0.8654	High Similarity	NPC26617
0.8641	High Similarity	NPC100487
0.8627	High Similarity	NPC472754
0.8627	High Similarity	NPC471148
0.8624	High Similarity	NPC471145
0.8614	High Similarity	NPC475949
0.8571	High Similarity	NPC475912
0.8571	High Similarity	NPC476300
0.8557	High Similarity	NPC51004
0.8544	High Similarity	NPC472755
0.8529	High Similarity	NPC46998
0.8529	High Similarity	NPC128733
0.8529	High Similarity	NPC264477
0.8529	High Similarity	NPC477511
0.8529	High Similarity	NPC110443
0.8529	High Similarity	NPC133907
0.8529	High Similarity	NPC185141
0.8515	High Similarity	NPC473326
0.85	High Similarity	NPC17585
0.85	High Similarity	NPC476315
0.8491	Intermediate Similarity	NPC38154
0.8469	Intermediate Similarity	NPC184463
0.8469	Intermediate Similarity	NPC30515
0.8462	Intermediate Similarity	NPC472756
0.8462	Intermediate Similarity	NPC477510
0.8462	Intermediate Similarity	NPC471143
0.8454	Intermediate Similarity	NPC307411
0.8438	Intermediate Similarity	NPC231889
0.8431	Intermediate Similarity	NPC477512
0.8411	Intermediate Similarity	NPC477103
0.84	Intermediate Similarity	NPC36954
0.84	Intermediate Similarity	NPC474947
0.84	Intermediate Similarity	NPC304886
0.8384	Intermediate Similarity	NPC469645
0.8384	Intermediate Similarity	NPC469692
0.8384	Intermediate Similarity	NPC179746
0.8384	Intermediate Similarity	NPC81419
0.8384	Intermediate Similarity	NPC135776
0.8381	Intermediate Similarity	NPC54737
0.8381	Intermediate Similarity	NPC9303
0.8381	Intermediate Similarity	NPC16313
0.8367	Intermediate Similarity	NPC475748
0.8351	Intermediate Similarity	NPC202672
0.835	Intermediate Similarity	NPC15993
0.8333	Intermediate Similarity	NPC141191
0.8333	Intermediate Similarity	NPC208233
0.8333	Intermediate Similarity	NPC473802
0.8333	Intermediate Similarity	NPC161855
0.8333	Intermediate Similarity	NPC474213
0.8318	Intermediate Similarity	NPC477102
0.8317	Intermediate Similarity	NPC76862
0.8317	Intermediate Similarity	NPC473291
0.8317	Intermediate Similarity	NPC39859
0.8317	Intermediate Similarity	NPC470883
0.8317	Intermediate Similarity	NPC230800
0.8317	Intermediate Similarity	NPC279621
0.8317	Intermediate Similarity	NPC158416
0.8317	Intermediate Similarity	NPC476275
0.8302	Intermediate Similarity	NPC324327
0.8302	Intermediate Similarity	NPC72813
0.8302	Intermediate Similarity	NPC194620
0.8302	Intermediate Similarity	NPC474421
0.8302	Intermediate Similarity	NPC326994
0.83	Intermediate Similarity	NPC121825
0.83	Intermediate Similarity	NPC477131
0.83	Intermediate Similarity	NPC471147
0.83	Intermediate Similarity	NPC303942
0.83	Intermediate Similarity	NPC140543
0.83	Intermediate Similarity	NPC473330
0.83	Intermediate Similarity	NPC473316
0.83	Intermediate Similarity	NPC476267
0.83	Intermediate Similarity	NPC57405
0.8283	Intermediate Similarity	NPC12172
0.8283	Intermediate Similarity	NPC300312
0.8283	Intermediate Similarity	NPC111114
0.8283	Intermediate Similarity	NPC476705
0.8283	Intermediate Similarity	NPC208886
0.8283	Intermediate Similarity	NPC261607
0.8269	Intermediate Similarity	NPC320019
0.8269	Intermediate Similarity	NPC324017
0.8269	Intermediate Similarity	NPC86077
0.8265	Intermediate Similarity	NPC151770
0.8265	Intermediate Similarity	NPC166919
0.8261	Intermediate Similarity	NPC473709
0.8261	Intermediate Similarity	NPC473919
0.8241	Intermediate Similarity	NPC257240
0.8241	Intermediate Similarity	NPC5103
0.8235	Intermediate Similarity	NPC169205
0.8235	Intermediate Similarity	NPC213947
0.8235	Intermediate Similarity	NPC108475
0.8235	Intermediate Similarity	NPC170143
0.8235	Intermediate Similarity	NPC40812
0.8235	Intermediate Similarity	NPC471140
0.8235	Intermediate Similarity	NPC474313
0.8224	Intermediate Similarity	NPC474664
0.8224	Intermediate Similarity	NPC117604
0.8224	Intermediate Similarity	NPC327286
0.8224	Intermediate Similarity	NPC55972
0.8224	Intermediate Similarity	NPC14862
0.8224	Intermediate Similarity	NPC169888
0.8224	Intermediate Similarity	NPC233379
0.8218	Intermediate Similarity	NPC107476
0.8218	Intermediate Similarity	NPC471141
0.8218	Intermediate Similarity	NPC48803
0.8218	Intermediate Similarity	NPC90121
0.8218	Intermediate Similarity	NPC193645
0.8218	Intermediate Similarity	NPC275960
0.8218	Intermediate Similarity	NPC471142
0.8214	Intermediate Similarity	NPC475401
0.8208	Intermediate Similarity	NPC475802
0.82	Intermediate Similarity	NPC125674
0.82	Intermediate Similarity	NPC162205
0.82	Intermediate Similarity	NPC288240
0.82	Intermediate Similarity	NPC295204
0.82	Intermediate Similarity	NPC273579
0.82	Intermediate Similarity	NPC228451
0.82	Intermediate Similarity	NPC475838
0.819	Intermediate Similarity	NPC4620
0.819	Intermediate Similarity	NPC471939
0.819	Intermediate Similarity	NPC472750
0.819	Intermediate Similarity	NPC472747
0.8182	Intermediate Similarity	NPC179394
0.8182	Intermediate Similarity	NPC473619
0.8182	Intermediate Similarity	NPC144133
0.8182	Intermediate Similarity	NPC476004
0.8182	Intermediate Similarity	NPC106395
0.8182	Intermediate Similarity	NPC469718
0.8182	Intermediate Similarity	NPC46269
0.8182	Intermediate Similarity	NPC474761
0.8182	Intermediate Similarity	NPC329857
0.8173	Intermediate Similarity	NPC171759
0.8165	Intermediate Similarity	NPC179798
0.8165	Intermediate Similarity	NPC304180
0.8163	Intermediate Similarity	NPC475902
0.8163	Intermediate Similarity	NPC476707
0.8163	Intermediate Similarity	NPC476706
0.8163	Intermediate Similarity	NPC281516
0.8155	Intermediate Similarity	NPC187761
0.8155	Intermediate Similarity	NPC83895
0.8155	Intermediate Similarity	NPC54843
0.8148	Intermediate Similarity	NPC59489
0.8148	Intermediate Similarity	NPC139838
0.8148	Intermediate Similarity	NPC15218
0.8144	Intermediate Similarity	NPC470242
0.8142	Intermediate Similarity	NPC477092
0.8137	Intermediate Similarity	NPC185553
0.8137	Intermediate Similarity	NPC477921
0.8137	Intermediate Similarity	NPC35498
0.8125	Intermediate Similarity	NPC475305
0.812	Intermediate Similarity	NPC471940
0.8119	Intermediate Similarity	NPC474247
0.8119	Intermediate Similarity	NPC167219
0.8119	Intermediate Similarity	NPC190294
0.8113	Intermediate Similarity	NPC475676
0.8113	Intermediate Similarity	NPC472748
0.8113	Intermediate Similarity	NPC220964
0.8108	Intermediate Similarity	NPC138303
0.8108	Intermediate Similarity	NPC67290
0.8108	Intermediate Similarity	NPC133677
0.81	Intermediate Similarity	NPC284185
0.81	Intermediate Similarity	NPC473321
0.81	Intermediate Similarity	NPC74103
0.81	Intermediate Similarity	NPC150978
0.81	Intermediate Similarity	NPC133698
0.81	Intermediate Similarity	NPC123177
0.81	Intermediate Similarity	NPC70595
0.8091	Intermediate Similarity	NPC138757
0.8091	Intermediate Similarity	NPC66108

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 NPC474741 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	1954
0.2-0.3	3713
0.3-0.4	2115
0.4-0.5	753
0.5-0.6	274
0.6-0.7	98
0.7-0.8	8
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8654	High Similarity	NPD7899	Clinical (unspecified phase)
0.8241	Intermediate Similarity	NPD6371	Approved
0.8218	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD46	Approved
0.7822	Intermediate Similarity	NPD6698	Approved
0.7723	Intermediate Similarity	NPD1695	Approved
0.7647	Intermediate Similarity	NPD7838	Discovery
0.7596	Intermediate Similarity	NPD5282	Discontinued
0.7573	Intermediate Similarity	NPD7983	Approved
0.7217	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7115	Discovery
0.7182	Intermediate Similarity	NPD5344	Discontinued
0.7156	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD5785	Approved
0.7025	Intermediate Similarity	NPD6319	Approved
0.7009	Intermediate Similarity	NPD5779	Approved
0.7009	Intermediate Similarity	NPD5778	Approved
0.6992	Remote Similarity	NPD7642	Approved
0.699	Remote Similarity	NPD5363	Approved
0.6967	Remote Similarity	NPD8515	Approved
0.6967	Remote Similarity	NPD8513	Phase 3
0.6967	Remote Similarity	NPD8517	Approved
0.6967	Remote Similarity	NPD8516	Approved
0.6957	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6686	Approved
0.6937	Remote Similarity	NPD6648	Approved
0.6923	Remote Similarity	NPD5786	Approved
0.687	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6053	Discontinued
0.6847	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4632	Approved
0.68	Remote Similarity	NPD7492	Approved
0.6765	Remote Similarity	NPD5369	Approved
0.6752	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6054	Approved
0.6746	Remote Similarity	NPD6616	Approved
0.672	Remote Similarity	NPD7830	Approved
0.672	Remote Similarity	NPD7829	Approved
0.6699	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6435	Approved
0.6699	Remote Similarity	NPD4269	Approved
0.6699	Remote Similarity	NPD4270	Approved
0.6699	Remote Similarity	NPD5209	Approved
0.6695	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6016	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6693	Remote Similarity	NPD7078	Approved
0.6693	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD1694	Approved
0.6641	Remote Similarity	NPD7736	Approved
0.664	Remote Similarity	NPD6370	Approved
0.664	Remote Similarity	NPD5988	Approved
0.6638	Remote Similarity	NPD6008	Approved
0.6615	Remote Similarity	NPD7260	Phase 2
0.6614	Remote Similarity	NPD8273	Phase 1
0.6604	Remote Similarity	NPD4249	Approved
0.6583	Remote Similarity	NPD8297	Approved
0.6581	Remote Similarity	NPD5697	Approved
0.6574	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6101	Approved
0.6555	Remote Similarity	NPD4634	Approved
0.6542	Remote Similarity	NPD4251	Approved
0.6542	Remote Similarity	NPD4250	Approved
0.6525	Remote Similarity	NPD6899	Approved
0.6525	Remote Similarity	NPD6881	Approved
0.6518	Remote Similarity	NPD7839	Suspended
0.6505	Remote Similarity	NPD4252	Approved
0.6505	Remote Similarity	NPD5368	Approved
0.6504	Remote Similarity	NPD6009	Approved
0.65	Remote Similarity	NPD2204	Approved
0.65	Remote Similarity	NPD6649	Approved
0.65	Remote Similarity	NPD6650	Approved
0.648	Remote Similarity	NPD6059	Approved
0.6476	Remote Similarity	NPD6110	Phase 1
0.6476	Remote Similarity	NPD7154	Phase 3
0.6471	Remote Similarity	NPD6013	Approved
0.6471	Remote Similarity	NPD6014	Approved
0.6471	Remote Similarity	NPD6012	Approved
0.6462	Remote Similarity	NPD7319	Approved
0.6457	Remote Similarity	NPD8328	Phase 3
0.6457	Remote Similarity	NPD7604	Phase 2
0.6455	Remote Similarity	NPD6411	Approved
0.6441	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8293	Discontinued
0.6429	Remote Similarity	NPD5983	Phase 2
0.6417	Remote Similarity	NPD7102	Approved
0.6417	Remote Similarity	NPD7290	Approved
0.6417	Remote Similarity	NPD6883	Approved
0.6387	Remote Similarity	NPD6011	Approved
0.6381	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6869	Approved
0.6364	Remote Similarity	NPD6847	Approved
0.6364	Remote Similarity	NPD8130	Phase 1
0.6364	Remote Similarity	NPD6617	Approved
0.6357	Remote Similarity	NPD8451	Approved
0.6357	Remote Similarity	NPD7507	Approved
0.6356	Remote Similarity	NPD7128	Approved
0.6356	Remote Similarity	NPD6675	Approved
0.6356	Remote Similarity	NPD6402	Approved
0.6356	Remote Similarity	NPD5739	Approved
0.6346	Remote Similarity	NPD4822	Approved
0.6346	Remote Similarity	NPD4819	Approved
0.6346	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4821	Approved
0.6346	Remote Similarity	NPD4820	Approved
0.6333	Remote Similarity	NPD6373	Approved
0.6333	Remote Similarity	NPD6372	Approved
0.6321	Remote Similarity	NPD5362	Discontinued
0.632	Remote Similarity	NPD7641	Discontinued
0.6316	Remote Similarity	NPD6845	Suspended
0.6311	Remote Similarity	NPD6882	Approved
0.6308	Remote Similarity	NPD8448	Approved
0.6303	Remote Similarity	NPD5701	Approved
0.6299	Remote Similarity	NPD8444	Approved
0.6299	Remote Similarity	NPD6921	Approved
0.6283	Remote Similarity	NPD5695	Phase 3
0.6261	Remote Similarity	NPD5696	Approved
0.6261	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8080	Discontinued
0.625	Remote Similarity	NPD7320	Approved
0.6239	Remote Similarity	NPD5211	Phase 2
0.6231	Remote Similarity	NPD6336	Discontinued
0.6207	Remote Similarity	NPD5286	Approved
0.6207	Remote Similarity	NPD5285	Approved
0.6207	Remote Similarity	NPD4696	Approved
0.6207	Remote Similarity	NPD7640	Approved
0.6207	Remote Similarity	NPD7639	Approved
0.6204	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6084	Phase 2
0.6174	Remote Similarity	NPD6083	Phase 2
0.6167	Remote Similarity	NPD6412	Phase 2
0.6165	Remote Similarity	NPD8391	Approved
0.6165	Remote Similarity	NPD8392	Approved
0.6165	Remote Similarity	NPD8390	Approved
0.6161	Remote Similarity	NPD7637	Suspended
0.6154	Remote Similarity	NPD4271	Approved
0.6154	Remote Similarity	NPD8342	Approved
0.6154	Remote Similarity	NPD8341	Approved
0.6154	Remote Similarity	NPD4268	Approved
0.6154	Remote Similarity	NPD8340	Approved
0.6154	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8299	Approved
0.6134	Remote Similarity	NPD5141	Approved
0.6111	Remote Similarity	NPD7500	Approved
0.6111	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6399	Phase 3
0.6102	Remote Similarity	NPD5224	Approved
0.6102	Remote Similarity	NPD5225	Approved
0.6102	Remote Similarity	NPD4633	Approved
0.6102	Remote Similarity	NPD5226	Approved
0.6058	Remote Similarity	NPD4756	Discovery
0.605	Remote Similarity	NPD5174	Approved
0.605	Remote Similarity	NPD5175	Approved
0.6047	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD5956	Approved
0.6034	Remote Similarity	NPD4755	Approved
0.6032	Remote Similarity	NPD6274	Approved
0.6018	Remote Similarity	NPD5693	Phase 1
0.6017	Remote Similarity	NPD5223	Approved
0.6016	Remote Similarity	NPD7100	Approved
0.6016	Remote Similarity	NPD7101	Approved
0.6015	Remote Similarity	NPD6033	Approved
0.6	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD4629	Approved
0.5985	Remote Similarity	NPD8415	Approved
0.5984	Remote Similarity	NPD6317	Approved
0.5982	Remote Similarity	NPD5370	Suspended
0.5968	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD5222	Approved
0.5948	Remote Similarity	NPD5221	Approved
0.5948	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6335	Approved
0.5938	Remote Similarity	NPD6314	Approved
0.5938	Remote Similarity	NPD6313	Approved
0.5932	Remote Similarity	NPD4700	Approved
0.5923	Remote Similarity	NPD8269	Approved
0.5923	Remote Similarity	NPD7503	Approved
0.5923	Remote Similarity	NPD8268	Approved
0.5923	Remote Similarity	NPD8266	Approved
0.5923	Remote Similarity	NPD8267	Approved
0.5897	Remote Similarity	NPD5173	Approved
0.5897	Remote Similarity	NPD7902	Approved
0.5893	Remote Similarity	NPD6672	Approved
0.5893	Remote Similarity	NPD5737	Approved
0.5891	Remote Similarity	NPD4522	Approved
0.5888	Remote Similarity	NPD4695	Discontinued
0.5887	Remote Similarity	NPD2067	Discontinued
0.5882	Remote Similarity	NPD1700	Approved
0.5877	Remote Similarity	NPD5284	Approved
0.5877	Remote Similarity	NPD5281	Approved
0.5877	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5331	Approved
0.5872	Remote Similarity	NPD5332	Approved
0.5859	Remote Similarity	NPD7331	Phase 2
0.5859	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4729	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