NPASS Compound

Structure

NPC118853 OpenBabel07101719142D 22 23 0 0 1 0 0 0 0 0999 V2000 0.3361 4.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3112 4.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5646 -0.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8966 3.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7227 1.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1190 2.1779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4554 2.6409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5203 2.9869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7227 1.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0646 2.8100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5203 0.2492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6420 3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0646 0.4261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 2.9271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 2.4271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4844 2.5316 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 16 2 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 11 2 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 19 2 0 0 0 0 14 17 2 0 0 0 0 14 22 1 0 0 0 0 18 15 1 6 0 0 0 19 22 1 0 0 0 0 20 4 1 1 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	344.398
LogP:	5.125
LogD:	4.538
LogS:	-5.532
# Rotatable Bonds:	1
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.734
Synthetic Accessibility Score:	5.628
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.569
MDCK Permeability:	2.945199958048761e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.06
20% Bioavailability (F20%):	0.239
30% Bioavailability (F30%):	0.76

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.267
Plasma Protein Binding (PPB):	90.61417388916016%
Volume Distribution (VD):	1.851
Pgp-substrate:	2.2813291549682617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.129
CYP1A2-substrate:	0.381
CYP2C19-inhibitor:	0.827
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.804
CYP2C9-substrate:	0.308
CYP2D6-inhibitor:	0.589
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.944
CYP3A4-substrate:	0.633

ADMET: Excretion

Clearance (CL):	7.718
Half-life (T1/2):	0.354

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.302
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.683
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.14
Carcinogencity:	0.188
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.106

Download Data

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

Natural Product: NPC118853

Natural Product ID:	NPC118853
*Common Name:**	Furanocembranoid 1
IUPAC Name:	(4S,5E,7S,10E)-7,11-dimethyl-4-propan-2-yl-14-oxabicyclo[11.2.1]hexadeca-1(15),5,10,13(16)-tetraen-7-ol
Synonyms:	Furanocembranoid 1
Standard InCHIKey:	SERTTYWXOQCADY-KKUMVBAPSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-15(2)18-8-7-17-13-19(22-14-17)12-16(3)6-5-10-20(4,21)11-9-18/h6,9,11,13-15,18,21H,5,7-8,10,12H2,1-4H3/b11-9+,16-6+/t18-,20+/m1/s1
SMILES:	CC(C)[C@@H]1CCc2cc(C/C(=C/CC[C@@](C)(/C=C/1)O)/C)oc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387650
PubChem CID:	16216160
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004144] Heteroaromatic compounds

*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	=	5.6	ug.mL-1	PMID[476398]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	6.3	ug.mL-1	PMID[476398]
NPT27	Others	Unspecified		IC50	=	7.8	ug.mL-1	PMID[476398]
NPT27	Others	Unspecified		IC50	=	7.0	ug.mL-1	PMID[476398]
NPT27	Others	Unspecified		IC50	=	5.9	ug.mL-1	PMID[476398]

☑ 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 NPC118853 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	262
0.1-0.2	1433
0.2-0.3	3636
0.3-0.4	9733
0.4-0.5	9948
0.5-0.6	6929
0.6-0.7	9233
0.7-0.8	1390
0.8-0.85	98
0.85-0.9	33
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9206	High Similarity	NPC106247
0.8992	High Similarity	NPC473268
0.8992	High Similarity	NPC187547
0.8992	High Similarity	NPC21831
0.8898	High Similarity	NPC473982
0.8898	High Similarity	NPC205523
0.888	High Similarity	NPC329707
0.8862	High Similarity	NPC243269
0.8819	High Similarity	NPC477645
0.879	High Similarity	NPC471074
0.879	High Similarity	NPC473885
0.875	High Similarity	NPC217180
0.875	High Similarity	NPC312525
0.875	High Similarity	NPC208906
0.875	High Similarity	NPC144745
0.873	High Similarity	NPC474279
0.873	High Similarity	NPC474438
0.8651	High Similarity	NPC290955
0.8644	High Similarity	NPC22678
0.8636	High Similarity	NPC472376
0.8618	High Similarity	NPC97566
0.8595	High Similarity	NPC227660
0.8583	High Similarity	NPC28054
0.8583	High Similarity	NPC279877
0.8571	High Similarity	NPC23086
0.8571	High Similarity	NPC202260
0.8561	High Similarity	NPC170604
0.8561	High Similarity	NPC215109
0.856	High Similarity	NPC188377
0.856	High Similarity	NPC65735
0.855	High Similarity	NPC265793
0.8548	High Similarity	NPC477967
0.8547	High Similarity	NPC177331
0.8519	High Similarity	NPC263337
0.8516	High Similarity	NPC59502
0.8512	High Similarity	NPC59035
0.8512	High Similarity	NPC474987
0.8512	High Similarity	NPC79202
0.8504	High Similarity	NPC476016
0.8504	High Similarity	NPC141059
0.8504	High Similarity	NPC246392
0.8496	Intermediate Similarity	NPC130976
0.8492	Intermediate Similarity	NPC75557
0.8492	Intermediate Similarity	NPC474829
0.8492	Intermediate Similarity	NPC71274
0.8468	Intermediate Similarity	NPC79557
0.8455	Intermediate Similarity	NPC137710
0.8455	Intermediate Similarity	NPC473969
0.8448	Intermediate Similarity	NPC42471
0.8438	Intermediate Similarity	NPC26532
0.8438	Intermediate Similarity	NPC112706
0.8438	Intermediate Similarity	NPC207294
0.843	Intermediate Similarity	NPC150895
0.8425	Intermediate Similarity	NPC138139
0.8425	Intermediate Similarity	NPC46536
0.8425	Intermediate Similarity	NPC329922
0.8425	Intermediate Similarity	NPC474260
0.8425	Intermediate Similarity	NPC81912
0.8425	Intermediate Similarity	NPC329694
0.8425	Intermediate Similarity	NPC83301
0.8421	Intermediate Similarity	NPC278832
0.8421	Intermediate Similarity	NPC307401
0.8421	Intermediate Similarity	NPC64157
0.8409	Intermediate Similarity	NPC159786
0.84	Intermediate Similarity	NPC473379
0.84	Intermediate Similarity	NPC471549
0.84	Intermediate Similarity	NPC263870
0.8385	Intermediate Similarity	NPC475092
0.8374	Intermediate Similarity	NPC291619
0.8374	Intermediate Similarity	NPC254958
0.8374	Intermediate Similarity	NPC243704
0.837	Intermediate Similarity	NPC473983
0.837	Intermediate Similarity	NPC148374
0.837	Intermediate Similarity	NPC201370
0.8361	Intermediate Similarity	NPC45536
0.8359	Intermediate Similarity	NPC83178
0.8359	Intermediate Similarity	NPC474830
0.8346	Intermediate Similarity	NPC303217
0.8333	Intermediate Similarity	NPC1811
0.8333	Intermediate Similarity	NPC476351
0.8333	Intermediate Similarity	NPC26157
0.8293	Intermediate Similarity	NPC131801
0.8271	Intermediate Similarity	NPC158525
0.8258	Intermediate Similarity	NPC474407
0.8258	Intermediate Similarity	NPC474426
0.8258	Intermediate Similarity	NPC474425
0.8254	Intermediate Similarity	NPC289911
0.8254	Intermediate Similarity	NPC283284
0.8244	Intermediate Similarity	NPC61788
0.8226	Intermediate Similarity	NPC206007
0.8211	Intermediate Similarity	NPC476031
0.8211	Intermediate Similarity	NPC476014
0.8209	Intermediate Similarity	NPC46896
0.8209	Intermediate Similarity	NPC204592
0.8203	Intermediate Similarity	NPC300098
0.8203	Intermediate Similarity	NPC471559
0.8189	Intermediate Similarity	NPC475818
0.8189	Intermediate Similarity	NPC16922
0.8175	Intermediate Similarity	NPC474136
0.8175	Intermediate Similarity	NPC115859
0.8168	Intermediate Similarity	NPC939
0.8162	Intermediate Similarity	NPC107571
0.814	Intermediate Similarity	NPC470858
0.8134	Intermediate Similarity	NPC476947
0.8134	Intermediate Similarity	NPC209858
0.813	Intermediate Similarity	NPC11821
0.8125	Intermediate Similarity	NPC477038
0.8125	Intermediate Similarity	NPC178382
0.8125	Intermediate Similarity	NPC477965
0.812	Intermediate Similarity	NPC293253
0.812	Intermediate Similarity	NPC218838
0.811	Intermediate Similarity	NPC317217
0.8106	Intermediate Similarity	NPC136340
0.8106	Intermediate Similarity	NPC89133
0.8099	Intermediate Similarity	NPC105249
0.808	Intermediate Similarity	NPC87466
0.8077	Intermediate Similarity	NPC184391
0.8077	Intermediate Similarity	NPC473355
0.8077	Intermediate Similarity	NPC471501
0.8077	Intermediate Similarity	NPC471573
0.8077	Intermediate Similarity	NPC471554
0.8071	Intermediate Similarity	NPC469642
0.8065	Intermediate Similarity	NPC76844
0.8062	Intermediate Similarity	NPC179354
0.8062	Intermediate Similarity	NPC290193
0.8045	Intermediate Similarity	NPC45358
0.8045	Intermediate Similarity	NPC471545
0.8045	Intermediate Similarity	NPC473344
0.8045	Intermediate Similarity	NPC471544
0.8045	Intermediate Similarity	NPC97740
0.8042	Intermediate Similarity	NPC228842
0.8042	Intermediate Similarity	NPC212257
0.8029	Intermediate Similarity	NPC62735
0.8028	Intermediate Similarity	NPC61284
0.8028	Intermediate Similarity	NPC113428
0.8017	Intermediate Similarity	NPC156768
0.8015	Intermediate Similarity	NPC477040
0.8015	Intermediate Similarity	NPC477123
0.8015	Intermediate Similarity	NPC477039
0.8015	Intermediate Similarity	NPC477966
0.8	Intermediate Similarity	NPC471521
0.8	Intermediate Similarity	NPC216810
0.8	Intermediate Similarity	NPC267004
0.8	Intermediate Similarity	NPC473356
0.8	Intermediate Similarity	NPC261733
0.8	Intermediate Similarity	NPC218712
0.8	Intermediate Similarity	NPC158871
0.8	Intermediate Similarity	NPC307346
0.8	Intermediate Similarity	NPC74612
0.7985	Intermediate Similarity	NPC470740
0.7984	Intermediate Similarity	NPC141252
0.7984	Intermediate Similarity	NPC11799
0.7971	Intermediate Similarity	NPC218204
0.7971	Intermediate Similarity	NPC61157
0.7971	Intermediate Similarity	NPC473681
0.797	Intermediate Similarity	NPC245395
0.797	Intermediate Similarity	NPC17681
0.7969	Intermediate Similarity	NPC174915
0.7969	Intermediate Similarity	NPC270807
0.7958	Intermediate Similarity	NPC308799
0.7956	Intermediate Similarity	NPC477534
0.7955	Intermediate Similarity	NPC50583
0.7955	Intermediate Similarity	NPC208389
0.7953	Intermediate Similarity	NPC474817
0.7953	Intermediate Similarity	NPC246214
0.7943	Intermediate Similarity	NPC247221
0.7929	Intermediate Similarity	NPC254198
0.7923	Intermediate Similarity	NPC221798
0.7914	Intermediate Similarity	NPC477537
0.791	Intermediate Similarity	NPC470976
0.791	Intermediate Similarity	NPC470977
0.791	Intermediate Similarity	NPC196979
0.7907	Intermediate Similarity	NPC272899
0.7903	Intermediate Similarity	NPC252004
0.7902	Intermediate Similarity	NPC93666
0.7899	Intermediate Similarity	NPC90953
0.7899	Intermediate Similarity	NPC233707
0.7895	Intermediate Similarity	NPC45947
0.7895	Intermediate Similarity	NPC476925
0.7891	Intermediate Similarity	NPC474542
0.7891	Intermediate Similarity	NPC1848
0.7883	Intermediate Similarity	NPC163029
0.7879	Intermediate Similarity	NPC476917
0.7879	Intermediate Similarity	NPC327527
0.7874	Intermediate Similarity	NPC4898
0.7868	Intermediate Similarity	NPC324117
0.7857	Intermediate Similarity	NPC52412
0.7852	Intermediate Similarity	NPC471006
0.7846	Intermediate Similarity	NPC130275
0.7842	Intermediate Similarity	NPC90296
0.7842	Intermediate Similarity	NPC282973
0.7842	Intermediate Similarity	NPC67003
0.7836	Intermediate Similarity	NPC282230
0.7836	Intermediate Similarity	NPC183348
0.7836	Intermediate Similarity	NPC298190
0.7829	Intermediate Similarity	NPC323118
0.7808	Intermediate Similarity	NPC121615
0.7808	Intermediate Similarity	NPC294511
0.7808	Intermediate Similarity	NPC474219
0.7808	Intermediate Similarity	NPC474378

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 NPC118853 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	1005
0.2-0.3	1460
0.3-0.4	2619
0.4-0.5	2098
0.5-0.6	1257
0.6-0.7	394
0.7-0.8	41
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
0.8296	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD2344	Approved
0.7823	Intermediate Similarity	NPD1241	Discontinued
0.7676	Intermediate Similarity	NPD2309	Approved
0.7669	Intermediate Similarity	NPD2798	Approved
0.7652	Intermediate Similarity	NPD1876	Approved
0.7626	Intermediate Similarity	NPD2799	Discontinued
0.7594	Intermediate Similarity	NPD2797	Approved
0.7557	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD3972	Approved
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7445	Intermediate Similarity	NPD3268	Approved
0.7442	Intermediate Similarity	NPD9092	Discovery
0.7413	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4308	Phase 3
0.7368	Intermediate Similarity	NPD1608	Approved
0.7353	Intermediate Similarity	NPD9494	Approved
0.7347	Intermediate Similarity	NPD6273	Approved
0.7319	Intermediate Similarity	NPD2313	Discontinued
0.7303	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6832	Phase 2
0.7286	Intermediate Similarity	NPD6355	Discontinued
0.7279	Intermediate Similarity	NPD5647	Approved
0.7273	Intermediate Similarity	NPD1471	Phase 3
0.7252	Intermediate Similarity	NPD9545	Approved
0.7237	Intermediate Similarity	NPD5761	Phase 2
0.7237	Intermediate Similarity	NPD5760	Phase 2
0.7214	Intermediate Similarity	NPD3142	Approved
0.7214	Intermediate Similarity	NPD3140	Approved
0.7206	Intermediate Similarity	NPD1203	Approved
0.7203	Intermediate Similarity	NPD1551	Phase 2
0.7203	Intermediate Similarity	NPD2796	Approved
0.7194	Intermediate Similarity	NPD3764	Approved
0.7171	Intermediate Similarity	NPD7577	Discontinued
0.7153	Intermediate Similarity	NPD2346	Discontinued
0.7153	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6002	Phase 3
0.7153	Intermediate Similarity	NPD6004	Phase 3
0.7153	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD2684	Approved
0.7143	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3750	Approved
0.7123	Intermediate Similarity	NPD7003	Approved
0.7121	Intermediate Similarity	NPD1894	Discontinued
0.712	Intermediate Similarity	NPD3134	Approved
0.7103	Intermediate Similarity	NPD1549	Phase 2
0.7099	Intermediate Similarity	NPD9493	Approved
0.7092	Intermediate Similarity	NPD1240	Approved
0.7092	Intermediate Similarity	NPD4307	Phase 2
0.709	Intermediate Similarity	NPD3496	Discontinued
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2935	Discontinued
0.708	Intermediate Similarity	NPD3266	Approved
0.708	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3267	Approved
0.7078	Intermediate Similarity	NPD2296	Approved
0.7077	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD411	Approved
0.7068	Intermediate Similarity	NPD5585	Approved
0.7067	Intermediate Similarity	NPD3873	Phase 3
0.7067	Intermediate Similarity	NPD920	Approved
0.7067	Intermediate Similarity	NPD3869	Phase 3
0.7059	Intermediate Similarity	NPD6280	Approved
0.7059	Intermediate Similarity	NPD6279	Approved
0.7047	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD447	Suspended
0.7034	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1019	Discontinued
0.7023	Intermediate Similarity	NPD7157	Approved
0.7023	Intermediate Similarity	NPD6671	Approved
0.7015	Intermediate Similarity	NPD1778	Approved
0.7015	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1510	Phase 2
0.7007	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1283	Approved
0.6994	Remote Similarity	NPD6765	Approved
0.6994	Remote Similarity	NPD6764	Approved
0.6993	Remote Similarity	NPD6653	Approved
0.6993	Remote Similarity	NPD1607	Approved
0.6988	Remote Similarity	NPD8434	Phase 2
0.6987	Remote Similarity	NPD3749	Approved
0.6977	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7458	Discontinued
0.6968	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6099	Approved
0.6966	Remote Similarity	NPD4477	Approved
0.6966	Remote Similarity	NPD6100	Approved
0.6966	Remote Similarity	NPD4476	Approved
0.6959	Remote Similarity	NPD3887	Approved
0.6959	Remote Similarity	NPD2354	Approved
0.6957	Remote Similarity	NPD6362	Approved
0.695	Remote Similarity	NPD6798	Discontinued
0.694	Remote Similarity	NPD1651	Approved
0.6939	Remote Similarity	NPD1243	Approved
0.6933	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4662	Approved
0.6933	Remote Similarity	NPD4661	Approved
0.6923	Remote Similarity	NPD3882	Suspended
0.6923	Remote Similarity	NPD7843	Approved
0.6923	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7440	Discontinued
0.6903	Remote Similarity	NPD7819	Suspended
0.6901	Remote Similarity	NPD8032	Phase 2
0.6897	Remote Similarity	NPD7033	Discontinued
0.6897	Remote Similarity	NPD3748	Approved
0.6892	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4110	Phase 3
0.6892	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6559	Discontinued
0.6889	Remote Similarity	NPD4626	Approved
0.6883	Remote Similarity	NPD7411	Suspended
0.6879	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2182	Approved
0.6871	Remote Similarity	NPD5958	Discontinued
0.6871	Remote Similarity	NPD2424	Discontinued
0.6867	Remote Similarity	NPD6799	Approved
0.6863	Remote Similarity	NPD2649	Approved
0.6863	Remote Similarity	NPD3226	Approved
0.6863	Remote Similarity	NPD2651	Approved
0.6861	Remote Similarity	NPD1481	Phase 2
0.685	Remote Similarity	NPD968	Approved
0.6831	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6784	Approved
0.6826	Remote Similarity	NPD6785	Approved
0.6825	Remote Similarity	NPD1237	Approved
0.6824	Remote Similarity	NPD2800	Approved
0.6821	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6599	Discontinued
0.6815	Remote Similarity	NPD5691	Approved
0.6815	Remote Similarity	NPD7768	Phase 2
0.6815	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4359	Approved
0.6809	Remote Similarity	NPD2614	Approved
0.6806	Remote Similarity	NPD4618	Approved
0.6806	Remote Similarity	NPD4622	Approved
0.6803	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2353	Approved
0.6797	Remote Similarity	NPD1358	Approved
0.6797	Remote Similarity	NPD290	Approved
0.6795	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD821	Approved
0.6788	Remote Similarity	NPD1281	Approved
0.6788	Remote Similarity	NPD1535	Discovery
0.6786	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6233	Phase 2
0.6783	Remote Similarity	NPD4062	Phase 3
0.6776	Remote Similarity	NPD5049	Phase 3
0.6772	Remote Similarity	NPD7075	Discontinued
0.6761	Remote Similarity	NPD7095	Approved
0.6757	Remote Similarity	NPD4534	Discontinued
0.6757	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2861	Phase 2
0.6738	Remote Similarity	NPD454	Approved
0.6738	Remote Similarity	NPD1712	Approved
0.6736	Remote Similarity	NPD2979	Phase 3
0.6736	Remote Similarity	NPD4060	Phase 1
0.6736	Remote Similarity	NPD4140	Approved
0.6735	Remote Similarity	NPD5712	Approved
0.6732	Remote Similarity	NPD5403	Approved
0.6731	Remote Similarity	NPD6844	Discontinued
0.6731	Remote Similarity	NPD1934	Approved
0.673	Remote Similarity	NPD919	Approved
0.6716	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3847	Discontinued
0.6714	Remote Similarity	NPD987	Approved
0.6712	Remote Similarity	NPD5688	Approved
0.6712	Remote Similarity	NPD5689	Approved
0.6711	Remote Similarity	NPD2533	Approved
0.6711	Remote Similarity	NPD2534	Approved
0.6711	Remote Similarity	NPD2532	Approved
0.671	Remote Similarity	NPD4380	Phase 2
0.6708	Remote Similarity	NPD6808	Phase 2
0.6693	Remote Similarity	NPD5909	Discontinued
0.6691	Remote Similarity	NPD4749	Approved
0.669	Remote Similarity	NPD1933	Approved
0.669	Remote Similarity	NPD4908	Phase 1
0.6688	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5494	Approved
0.6667	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1610	Phase 2
0.6667	Remote Similarity	NPD5536	Phase 2
0.6667	Remote Similarity	NPD5535	Approved
0.6646	Remote Similarity	NPD1247	Approved
0.6643	Remote Similarity	NPD3225	Approved
0.6643	Remote Similarity	NPD6696	Suspended
0.6642	Remote Similarity	NPD3019	Approved
0.6642	Remote Similarity	NPD2932	Approved
0.6642	Remote Similarity	NPD2668	Approved
0.6642	Remote Similarity	NPD2667	Approved
0.6641	Remote Similarity	NPD9697	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