NPASS Compound

Structure

NPC473448 OpenBabel07101718242D 25 26 0 0 1 0 0 0 0 0999 V2000 1.7892 2.8323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2173 3.3430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2949 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5432 -1.6011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0177 1.7834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5017 1.6146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0339 1.4532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0339 -0.4989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3549 1.0114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3549 -0.0571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4685 0.4771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5017 -0.6603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8558 2.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5609 1.7263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9076 1.2492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9076 -0.2949 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5609 -0.7720 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4685 0.4771 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0177 -0.8291 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8558 -1.6796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5440 2.0761 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2949 0.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4059 -1.7009 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 13 1 0 0 0 0 2 13 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 14 13 1 1 0 0 0 15 18 1 0 0 0 0 16 11 1 1 0 0 0 16 25 1 0 0 0 0 17 20 1 1 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 3 1 6 0 0 0 19 23 1 0 0 0 0 20 4 1 6 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.22
Volume:	373.405
LogP:	3.019
LogD:	2.436
LogS:	-3.474
# Rotatable Bonds:	1
TPSA:	94.06
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	5.849
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.821
MDCK Permeability:	1.1505739166750573e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.229
Human Intestinal Absorption (HIA):	0.08
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.475
Plasma Protein Binding (PPB):	89.5694351196289%
Volume Distribution (VD):	2.294
Pgp-substrate:	4.762241363525391%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.392
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.504
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.603
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.529
CYP3A4-substrate:	0.479

ADMET: Excretion

Clearance (CL):	9.976
Half-life (T1/2):	0.603

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.342
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.84
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.137
Carcinogencity:	0.726
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.397

Download Data

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

Natural Product: NPC473448

Natural Product ID:	NPC473448
*Common Name:**	Furanocembranoid 4
IUPAC Name:	(1S,3S,4R,7S,8E,10S)-3,4,7-trihydroxy-3,7-dimethyl-10-propan-2-yl-15-oxabicyclo[11.2.1]hexadeca-8,13(16)-dien-14-one
Synonyms:	Furanocembranoid 4
Standard InCHIKey:	ZXUDZQNLOBXDTI-CLCGKSASSA-N
Standard InCHI:	InChI=1S/C20H32O5/c1-13(2)14-5-6-15-11-16(25-18(15)22)12-20(4,24)17(21)8-10-19(3,23)9-7-14/h7,9,11,13-14,16-17,21,23-24H,5-6,8,10,12H2,1-4H3/b9-7+/t14-,16-,17-,19-,20+/m1/s1
SMILES:	CC(C)C1CCC2=CC(CC(C(CCC(C=C1)(C)O)O)(C)O)OC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL436533
PubChem CID:	44421682
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
NPO16932	Croton oblongifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479328]
NPO16932	Croton oblongifolius	Species	Euphorbiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17341114]
NPO16932	Croton oblongifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16932	Croton oblongifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	6.1	ug.mL-1	PMID[564524]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	6.0	ug.mL-1	PMID[564524]
NPT27	Others	Unspecified		IC50	=	9.6	ug.mL-1	PMID[564524]
NPT27	Others	Unspecified		IC50	=	9.3	ug.mL-1	PMID[564524]
NPT27	Others	Unspecified		IC50	=	8.1	ug.mL-1	PMID[564524]

☑ 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 NPC473448 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	199
0.1-0.2	1067
0.2-0.3	4167
0.3-0.4	7546
0.4-0.5	15488
0.5-0.6	7670
0.6-0.7	4767
0.7-0.8	1674
0.8-0.85	114
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8736	High Similarity	NPC137033
0.8706	High Similarity	NPC325031
0.8696	High Similarity	NPC304886
0.8696	High Similarity	NPC36954
0.8681	High Similarity	NPC475912
0.8667	High Similarity	NPC475855
0.8667	High Similarity	NPC474761
0.8667	High Similarity	NPC476004
0.8571	High Similarity	NPC30515
0.8571	High Similarity	NPC184463
0.8539	High Similarity	NPC160138
0.8511	High Similarity	NPC40812
0.8506	High Similarity	NPC11620
0.8495	Intermediate Similarity	NPC270013
0.8495	Intermediate Similarity	NPC14961
0.8495	Intermediate Similarity	NPC272050
0.8478	Intermediate Similarity	NPC228451
0.8478	Intermediate Similarity	NPC475838
0.8478	Intermediate Similarity	NPC476300
0.8478	Intermediate Similarity	NPC125674
0.8462	Intermediate Similarity	NPC51004
0.8462	Intermediate Similarity	NPC144133
0.8462	Intermediate Similarity	NPC179394
0.8444	Intermediate Similarity	NPC202672
0.8444	Intermediate Similarity	NPC153805
0.8444	Intermediate Similarity	NPC474471
0.8444	Intermediate Similarity	NPC227379
0.8438	Intermediate Similarity	NPC150923
0.8427	Intermediate Similarity	NPC164393
0.8427	Intermediate Similarity	NPC469483
0.8427	Intermediate Similarity	NPC305475
0.8427	Intermediate Similarity	NPC475461
0.8421	Intermediate Similarity	NPC83895
0.8421	Intermediate Similarity	NPC187268
0.8421	Intermediate Similarity	NPC187761
0.8409	Intermediate Similarity	NPC163093
0.8404	Intermediate Similarity	NPC476315
0.8404	Intermediate Similarity	NPC279621
0.8391	Intermediate Similarity	NPC474291
0.8387	Intermediate Similarity	NPC474247
0.8387	Intermediate Similarity	NPC474035
0.8387	Intermediate Similarity	NPC81386
0.837	Intermediate Similarity	NPC476705
0.8352	Intermediate Similarity	NPC295312
0.8352	Intermediate Similarity	NPC307411
0.8351	Intermediate Similarity	NPC86077
0.8333	Intermediate Similarity	NPC475053
0.8333	Intermediate Similarity	NPC248602
0.8315	Intermediate Similarity	NPC477014
0.8315	Intermediate Similarity	NPC477013
0.8315	Intermediate Similarity	NPC322529
0.8315	Intermediate Similarity	NPC255307
0.8315	Intermediate Similarity	NPC261380
0.8315	Intermediate Similarity	NPC120398
0.8315	Intermediate Similarity	NPC471567
0.8295	Intermediate Similarity	NPC250315
0.8295	Intermediate Similarity	NPC253801
0.828	Intermediate Similarity	NPC295204
0.828	Intermediate Similarity	NPC288240
0.828	Intermediate Similarity	NPC212486
0.828	Intermediate Similarity	NPC476049
0.828	Intermediate Similarity	NPC273579
0.828	Intermediate Similarity	NPC162205
0.828	Intermediate Similarity	NPC81419
0.828	Intermediate Similarity	NPC179746
0.8265	Intermediate Similarity	NPC472755
0.8265	Intermediate Similarity	NPC475945
0.8265	Intermediate Similarity	NPC475871
0.8247	Intermediate Similarity	NPC472753
0.8242	Intermediate Similarity	NPC476803
0.8229	Intermediate Similarity	NPC255592
0.8229	Intermediate Similarity	NPC261377
0.8229	Intermediate Similarity	NPC473326
0.8229	Intermediate Similarity	NPC222303
0.8229	Intermediate Similarity	NPC308567
0.8222	Intermediate Similarity	NPC279267
0.8222	Intermediate Similarity	NPC69082
0.8222	Intermediate Similarity	NPC311163
0.8222	Intermediate Similarity	NPC477015
0.8214	Intermediate Similarity	NPC329852
0.8211	Intermediate Similarity	NPC234993
0.8211	Intermediate Similarity	NPC230800
0.8211	Intermediate Similarity	NPC134072
0.8202	Intermediate Similarity	NPC243618
0.8202	Intermediate Similarity	NPC474776
0.8202	Intermediate Similarity	NPC70424
0.8202	Intermediate Similarity	NPC191476
0.8202	Intermediate Similarity	NPC474780
0.8202	Intermediate Similarity	NPC114979
0.8202	Intermediate Similarity	NPC156804
0.8202	Intermediate Similarity	NPC476804
0.8202	Intermediate Similarity	NPC82297
0.8202	Intermediate Similarity	NPC9868
0.82	Intermediate Similarity	NPC187435
0.82	Intermediate Similarity	NPC67321
0.8191	Intermediate Similarity	NPC65829
0.8191	Intermediate Similarity	NPC477131
0.8191	Intermediate Similarity	NPC474338
0.8182	Intermediate Similarity	NPC473780
0.8182	Intermediate Similarity	NPC145914
0.8182	Intermediate Similarity	NPC11332
0.8182	Intermediate Similarity	NPC131002
0.8182	Intermediate Similarity	NPC65930
0.8182	Intermediate Similarity	NPC94875
0.8182	Intermediate Similarity	NPC73310
0.8182	Intermediate Similarity	NPC473712
0.8182	Intermediate Similarity	NPC329829
0.8182	Intermediate Similarity	NPC473529
0.8182	Intermediate Similarity	NPC475159
0.8182	Intermediate Similarity	NPC180363
0.8172	Intermediate Similarity	NPC208886
0.8172	Intermediate Similarity	NPC473321
0.8172	Intermediate Similarity	NPC12172
0.8163	Intermediate Similarity	NPC472754
0.8163	Intermediate Similarity	NPC474747
0.8152	Intermediate Similarity	NPC212598
0.8152	Intermediate Similarity	NPC133450
0.8152	Intermediate Similarity	NPC473564
0.8144	Intermediate Similarity	NPC288876
0.814	Intermediate Similarity	NPC192006
0.8132	Intermediate Similarity	NPC178215
0.8132	Intermediate Similarity	NPC474765
0.8125	Intermediate Similarity	NPC471462
0.8111	Intermediate Similarity	NPC110710
0.8111	Intermediate Similarity	NPC132496
0.8111	Intermediate Similarity	NPC329615
0.8111	Intermediate Similarity	NPC66346
0.8111	Intermediate Similarity	NPC165162
0.8111	Intermediate Similarity	NPC223871
0.8111	Intermediate Similarity	NPC329838
0.8111	Intermediate Similarity	NPC283085
0.8111	Intermediate Similarity	NPC82795
0.8111	Intermediate Similarity	NPC1083
0.8111	Intermediate Similarity	NPC473478
0.8111	Intermediate Similarity	NPC215364
0.8111	Intermediate Similarity	NPC103284
0.8111	Intermediate Similarity	NPC473651
0.8111	Intermediate Similarity	NPC473669
0.8111	Intermediate Similarity	NPC231009
0.8111	Intermediate Similarity	NPC21469
0.8111	Intermediate Similarity	NPC107986
0.8111	Intermediate Similarity	NPC182383
0.8111	Intermediate Similarity	NPC286338
0.8105	Intermediate Similarity	NPC471141
0.81	Intermediate Similarity	NPC472751
0.81	Intermediate Similarity	NPC243998
0.81	Intermediate Similarity	NPC472749
0.8095	Intermediate Similarity	NPC474758
0.809	Intermediate Similarity	NPC131669
0.809	Intermediate Similarity	NPC473390
0.809	Intermediate Similarity	NPC169575
0.809	Intermediate Similarity	NPC144415
0.809	Intermediate Similarity	NPC40746
0.8085	Intermediate Similarity	NPC469645
0.8085	Intermediate Similarity	NPC469692
0.8081	Intermediate Similarity	NPC110989
0.8081	Intermediate Similarity	NPC472747
0.8081	Intermediate Similarity	NPC472750
0.8068	Intermediate Similarity	NPC471325
0.8068	Intermediate Similarity	NPC112868
0.8065	Intermediate Similarity	NPC469368
0.8065	Intermediate Similarity	NPC177668
0.8065	Intermediate Similarity	NPC3952
0.8065	Intermediate Similarity	NPC473619
0.8061	Intermediate Similarity	NPC474742
0.8046	Intermediate Similarity	NPC55304
0.8046	Intermediate Similarity	NPC226226
0.8043	Intermediate Similarity	NPC476706
0.8043	Intermediate Similarity	NPC473905
0.8043	Intermediate Similarity	NPC48338
0.8043	Intermediate Similarity	NPC280621
0.8043	Intermediate Similarity	NPC320458
0.8043	Intermediate Similarity	NPC473715
0.8043	Intermediate Similarity	NPC21208
0.8043	Intermediate Similarity	NPC89001
0.8043	Intermediate Similarity	NPC20339
0.8043	Intermediate Similarity	NPC233551
0.8043	Intermediate Similarity	NPC476707
0.8043	Intermediate Similarity	NPC476704
0.8043	Intermediate Similarity	NPC476805
0.8043	Intermediate Similarity	NPC40376
0.8043	Intermediate Similarity	NPC281516
0.8041	Intermediate Similarity	NPC474213
0.8022	Intermediate Similarity	NPC232555
0.8022	Intermediate Similarity	NPC103523
0.8022	Intermediate Similarity	NPC134865
0.8022	Intermediate Similarity	NPC261721
0.8022	Intermediate Similarity	NPC474949
0.8022	Intermediate Similarity	NPC134807
0.8022	Intermediate Similarity	NPC231096
0.8022	Intermediate Similarity	NPC47937
0.8022	Intermediate Similarity	NPC142117
0.8022	Intermediate Similarity	NPC473687
0.8022	Intermediate Similarity	NPC112685
0.8022	Intermediate Similarity	NPC293136
0.8022	Intermediate Similarity	NPC210218
0.8022	Intermediate Similarity	NPC62118
0.8022	Intermediate Similarity	NPC204686
0.8022	Intermediate Similarity	NPC122502
0.8022	Intermediate Similarity	NPC241360

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 NPC473448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1606
0.2-0.3	3535
0.3-0.4	2417
0.4-0.5	947
0.5-0.6	346
0.6-0.7	100
0.7-0.8	22
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
0.8261	Intermediate Similarity	NPD46	Approved
0.8261	Intermediate Similarity	NPD6698	Approved
0.8065	Intermediate Similarity	NPD7838	Discovery
0.7961	Intermediate Similarity	NPD6371	Approved
0.7941	Intermediate Similarity	NPD6686	Approved
0.7843	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD7983	Approved
0.77	Intermediate Similarity	NPD5344	Discontinued
0.7692	Intermediate Similarity	NPD7154	Phase 3
0.7684	Intermediate Similarity	NPD5785	Approved
0.7556	Intermediate Similarity	NPD4821	Approved
0.7556	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4819	Approved
0.7556	Intermediate Similarity	NPD4820	Approved
0.7556	Intermediate Similarity	NPD4822	Approved
0.7551	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5363	Approved
0.7526	Intermediate Similarity	NPD5778	Approved
0.7526	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5362	Discontinued
0.7391	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6435	Approved
0.7383	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4251	Approved
0.7368	Intermediate Similarity	NPD4250	Approved
0.7333	Intermediate Similarity	NPD4271	Approved
0.7333	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4268	Approved
0.7327	Intermediate Similarity	NPD4225	Approved
0.7263	Intermediate Similarity	NPD4249	Approved
0.7255	Intermediate Similarity	NPD7639	Approved
0.7255	Intermediate Similarity	NPD6648	Approved
0.7255	Intermediate Similarity	NPD7640	Approved
0.7216	Intermediate Similarity	NPD1695	Approved
0.7207	Intermediate Similarity	NPD7115	Discovery
0.7204	Intermediate Similarity	NPD4269	Approved
0.7204	Intermediate Similarity	NPD4270	Approved
0.7196	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5368	Approved
0.7158	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7638	Approved
0.7156	Intermediate Similarity	NPD6053	Discontinued
0.7097	Intermediate Similarity	NPD5369	Approved
0.7083	Intermediate Similarity	NPD5786	Approved
0.6989	Remote Similarity	NPD4252	Approved
0.6979	Remote Similarity	NPD1694	Approved
0.6961	Remote Similarity	NPD7839	Suspended
0.6947	Remote Similarity	NPD5331	Approved
0.6947	Remote Similarity	NPD5332	Approved
0.6931	Remote Similarity	NPD5282	Discontinued
0.6915	Remote Similarity	NPD4790	Discontinued
0.69	Remote Similarity	NPD7637	Suspended
0.6875	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6101	Approved
0.6869	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7507	Approved
0.6842	Remote Similarity	NPD5209	Approved
0.6818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.681	Remote Similarity	NPD8517	Approved
0.681	Remote Similarity	NPD8516	Approved
0.681	Remote Similarity	NPD8515	Approved
0.681	Remote Similarity	NPD8513	Phase 3
0.6789	Remote Similarity	NPD6881	Approved
0.6789	Remote Similarity	NPD6899	Approved
0.6744	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6411	Approved
0.6731	Remote Similarity	NPD6083	Phase 2
0.6731	Remote Similarity	NPD6084	Phase 2
0.6697	Remote Similarity	NPD6412	Phase 2
0.6697	Remote Similarity	NPD5697	Approved
0.6696	Remote Similarity	NPD8297	Approved
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6637	Remote Similarity	NPD4632	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.663	Remote Similarity	NPD8039	Approved
0.6628	Remote Similarity	NPD3197	Phase 1
0.6607	Remote Similarity	NPD6847	Approved
0.6607	Remote Similarity	NPD8130	Phase 1
0.6607	Remote Similarity	NPD6650	Approved
0.6607	Remote Similarity	NPD6869	Approved
0.6607	Remote Similarity	NPD6617	Approved
0.6607	Remote Similarity	NPD6649	Approved
0.6606	Remote Similarity	NPD6675	Approved
0.6606	Remote Similarity	NPD7128	Approved
0.6606	Remote Similarity	NPD6402	Approved
0.6606	Remote Similarity	NPD5739	Approved
0.6598	Remote Similarity	NPD6110	Phase 1
0.6581	Remote Similarity	NPD6319	Approved
0.6577	Remote Similarity	NPD6012	Approved
0.6577	Remote Similarity	NPD6014	Approved
0.6577	Remote Similarity	NPD6013	Approved
0.6552	Remote Similarity	NPD7328	Approved
0.6552	Remote Similarity	NPD7327	Approved
0.6549	Remote Similarity	NPD6882	Approved
0.6545	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5695	Phase 3
0.6531	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD8074	Phase 3
0.6525	Remote Similarity	NPD7503	Approved
0.6505	Remote Similarity	NPD6399	Phase 3
0.65	Remote Similarity	NPD7524	Approved
0.6496	Remote Similarity	NPD7516	Approved
0.6486	Remote Similarity	NPD7320	Approved
0.6486	Remote Similarity	NPD6011	Approved
0.6486	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5211	Phase 2
0.6457	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD8273	Phase 1
0.6442	Remote Similarity	NPD7748	Approved
0.6441	Remote Similarity	NPD8377	Approved
0.6441	Remote Similarity	NPD8294	Approved
0.6429	Remote Similarity	NPD6695	Phase 3
0.6429	Remote Similarity	NPD6372	Approved
0.6429	Remote Similarity	NPD6373	Approved
0.6422	Remote Similarity	NPD6647	Phase 2
0.6417	Remote Similarity	NPD7829	Approved
0.6417	Remote Similarity	NPD7642	Approved
0.6417	Remote Similarity	NPD7830	Approved
0.6415	Remote Similarity	NPD7902	Approved
0.6408	Remote Similarity	NPD7515	Phase 2
0.6404	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7334	Approved
0.64	Remote Similarity	NPD7521	Approved
0.64	Remote Similarity	NPD6409	Approved
0.64	Remote Similarity	NPD6684	Approved
0.64	Remote Similarity	NPD5330	Approved
0.64	Remote Similarity	NPD7146	Approved
0.6396	Remote Similarity	NPD5701	Approved
0.6387	Remote Similarity	NPD8033	Approved
0.6387	Remote Similarity	NPD8335	Approved
0.6387	Remote Similarity	NPD8379	Approved
0.6387	Remote Similarity	NPD8380	Approved
0.6387	Remote Similarity	NPD8296	Approved
0.6387	Remote Similarity	NPD8378	Approved
0.6373	Remote Similarity	NPD5370	Suspended
0.6372	Remote Similarity	NPD4634	Approved
0.6364	Remote Similarity	NPD7492	Approved
0.6364	Remote Similarity	NPD5141	Approved
0.6355	Remote Similarity	NPD5696	Approved
0.6348	Remote Similarity	NPD8133	Approved
0.6327	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6009	Approved
0.6325	Remote Similarity	NPD7505	Discontinued
0.6321	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4756	Discovery
0.6316	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6616	Approved
0.6303	Remote Similarity	NPD6054	Approved
0.6296	Remote Similarity	NPD4696	Approved
0.6296	Remote Similarity	NPD5286	Approved
0.6296	Remote Similarity	NPD5285	Approved
0.6292	Remote Similarity	NPD7331	Phase 2
0.6281	Remote Similarity	NPD7604	Phase 2
0.6279	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6672	Approved
0.6275	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5737	Approved
0.6275	Remote Similarity	NPD6903	Approved
0.6271	Remote Similarity	NPD7641	Discontinued
0.626	Remote Similarity	NPD7078	Approved
0.625	Remote Similarity	NPD6685	Approved
0.625	Remote Similarity	NPD6079	Approved
0.625	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD5983	Phase 2
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5281	Approved
0.6238	Remote Similarity	NPD4519	Discontinued
0.6238	Remote Similarity	NPD4623	Approved
0.6228	Remote Similarity	NPD6421	Discontinued
0.6226	Remote Similarity	NPD4629	Approved
0.6226	Remote Similarity	NPD5210	Approved
0.6218	Remote Similarity	NPD7101	Approved
0.6218	Remote Similarity	NPD7100	Approved
0.6214	Remote Similarity	NPD4753	Phase 2
0.621	Remote Similarity	NPD7736	Approved
0.62	Remote Similarity	NPD3666	Approved
0.62	Remote Similarity	NPD3665	Phase 1
0.62	Remote Similarity	NPD3133	Approved
0.6198	Remote Similarity	NPD6370	Approved
0.619	Remote Similarity	NPD7260	Phase 2
0.6186	Remote Similarity	NPD7500	Approved
0.6182	Remote Similarity	NPD5226	Approved
0.6182	Remote Similarity	NPD5225	Approved
0.6182	Remote Similarity	NPD4633	Approved
0.6182	Remote Similarity	NPD5224	Approved
0.618	Remote Similarity	NPD7341	Phase 2
0.6179	Remote Similarity	NPD6336	Discontinued
0.6179	Remote Similarity	NPD8451	Approved
0.6176	Remote Similarity	NPD7750	Discontinued
0.6174	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6335	Approved
0.6132	Remote Similarity	NPD7900	Approved
0.6132	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD8448	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