NPASS Compound

Structure

NPC61788 OpenBabel07101718202D 23 25 0 0 1 0 0 0 0 0999 V2000 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4161 -0.8188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2548 -0.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9973 0.7441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 -0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6390 -0.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -0.6628 -1.6002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9960 0.6918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 18 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 10 23 1 0 0 0 0 11 17 1 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 6 0 0 0 17 22 1 6 0 0 0 18 19 1 6 0 0 0 18 20 1 0 0 0 0 19 3 1 6 0 0 0 20 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	3.394
LogD:	3.027
LogS:	-4.134
# Rotatable Bonds:	4
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.826
Synthetic Accessibility Score:	4.717
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.496
MDCK Permeability:	1.2796127521141898e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.401
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.734
30% Bioavailability (F30%):	0.48

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.417
Plasma Protein Binding (PPB):	96.627685546875%
Volume Distribution (VD):	2.406
Pgp-substrate:	3.6740314960479736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.355
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.226
CYP2C19-substrate:	0.554
CYP2C9-inhibitor:	0.446
CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.336
CYP2D6-substrate:	0.255
CYP3A4-inhibitor:	0.852
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	13.003
Half-life (T1/2):	0.407

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.374
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.927
Maximum Recommended Daily Dose:	0.279
Skin Sensitization:	0.171
Carcinogencity:	0.899
Eye Corrosion:	0.13
Eye Irritation:	0.623
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC61788

Natural Product ID:	NPC61788
*Common Name:**	7Alpha,20-Dihydroxyannonene
IUPAC Name:	(2R,3S,4S,4aS,8aR)-4-[2-(furan-3-yl)ethyl]-4-(hydroxymethyl)-3,8,8a-trimethyl-1,2,3,4a,5,6-hexahydronaphthalen-2-ol
Synonyms:	7Alpha,20-Dihydroxyannonene
Standard InCHIKey:	DCLPBMPTOFSZFT-LFZDHENXSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-14-5-4-6-18-19(14,3)11-17(22)15(2)20(18,13-21)9-7-16-8-10-23-12-16/h5,8,10,12,15,17-18,21-22H,4,6-7,9,11,13H2,1-3H3/t15-,17-,18+,19+,20-/m1/s1
SMILES:	OC[C@]1(CCc2cocc2)[C@H](C)[C@H](O)C[C@@]2([C@@H]1CCC=C2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL475560
PubChem CID:	25195057
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO32668	ptychopetalum olacoides	Species	Olacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18821798]
NPO32668	ptychopetalum olacoides	Species	Olacaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[19095451]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	236.3	um	PMID[454556]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	106.5	um	PMID[454556]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	101.7	um	PMID[454556]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	95.3	um	PMID[454556]

☑ 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 NPC61788 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	251
0.1-0.2	1192
0.2-0.3	2592
0.3-0.4	5788
0.4-0.5	11744
0.5-0.6	10315
0.6-0.7	9617
0.7-0.8	955
0.8-0.85	157
0.85-0.9	73
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9683	High Similarity	NPC218838
0.9435	High Similarity	NPC23086
0.938	High Similarity	NPC476947
0.9173	High Similarity	NPC67003
0.9134	High Similarity	NPC207294
0.9134	High Similarity	NPC112706
0.9113	High Similarity	NPC477967
0.9055	High Similarity	NPC83178
0.8976	High Similarity	NPC138139
0.8976	High Similarity	NPC46536
0.8971	High Similarity	NPC476946
0.8955	High Similarity	NPC90953
0.8939	High Similarity	NPC158525
0.8923	High Similarity	NPC298190
0.8915	High Similarity	NPC59502
0.8906	High Similarity	NPC290955
0.8898	High Similarity	NPC290193
0.8897	High Similarity	NPC121158
0.8897	High Similarity	NPC52412
0.8872	High Similarity	NPC46896
0.8841	High Similarity	NPC5676
0.8841	High Similarity	NPC185456
0.8837	High Similarity	NPC477123
0.8837	High Similarity	NPC477966
0.8832	High Similarity	NPC243577
0.8815	High Similarity	NPC202260
0.879	High Similarity	NPC243704
0.8779	High Similarity	NPC89133
0.8768	High Similarity	NPC251865
0.8768	High Similarity	NPC476944
0.876	High Similarity	NPC246392
0.875	High Similarity	NPC300098
0.874	High Similarity	NPC272899
0.874	High Similarity	NPC16922
0.8723	High Similarity	NPC470998
0.8714	High Similarity	NPC471174
0.8714	High Similarity	NPC302987
0.8712	High Similarity	NPC473982
0.8699	High Similarity	NPC150895
0.8692	High Similarity	NPC279877
0.8692	High Similarity	NPC329707
0.8692	High Similarity	NPC477039
0.8692	High Similarity	NPC477040
0.8692	High Similarity	NPC26532
0.8686	High Similarity	NPC205765
0.8667	High Similarity	NPC4764
0.8667	High Similarity	NPC470742
0.8662	High Similarity	NPC470997
0.8652	High Similarity	NPC471007
0.8643	High Similarity	NPC346
0.8623	High Similarity	NPC263337
0.8613	High Similarity	NPC56197
0.8613	High Similarity	NPC90296
0.8605	High Similarity	NPC303010
0.8605	High Similarity	NPC179354
0.8603	High Similarity	NPC471996
0.8592	High Similarity	NPC69647
0.8592	High Similarity	NPC234494
0.8592	High Similarity	NPC125182
0.8592	High Similarity	NPC472654
0.8592	High Similarity	NPC195325
0.8582	High Similarity	NPC216755
0.8582	High Similarity	NPC255414
0.8571	High Similarity	NPC471995
0.8561	High Similarity	NPC476925
0.855	High Similarity	NPC327527
0.855	High Similarity	NPC476917
0.8542	High Similarity	NPC469503
0.8542	High Similarity	NPC33938
0.8538	High Similarity	NPC74612
0.8531	High Similarity	NPC196846
0.8529	High Similarity	NPC310830
0.8529	High Similarity	NPC307401
0.8527	High Similarity	NPC130275
0.8527	High Similarity	NPC477038
0.8527	High Similarity	NPC477965
0.8519	High Similarity	NPC92941
0.8516	High Similarity	NPC317217
0.8507	High Similarity	NPC471006
0.8485	Intermediate Similarity	NPC198904
0.8483	Intermediate Similarity	NPC178932
0.8483	Intermediate Similarity	NPC57998
0.8467	Intermediate Similarity	NPC236532
0.8467	Intermediate Similarity	NPC472376
0.8456	Intermediate Similarity	NPC146872
0.8451	Intermediate Similarity	NPC250228
0.8429	Intermediate Similarity	NPC267632
0.8425	Intermediate Similarity	NPC35000
0.8425	Intermediate Similarity	NPC92979
0.8425	Intermediate Similarity	NPC469336
0.8414	Intermediate Similarity	NPC476939
0.8414	Intermediate Similarity	NPC472672
0.8414	Intermediate Similarity	NPC476940
0.8414	Intermediate Similarity	NPC470996
0.8413	Intermediate Similarity	NPC212918
0.8392	Intermediate Similarity	NPC476941
0.8392	Intermediate Similarity	NPC476942
0.8385	Intermediate Similarity	NPC243269
0.8385	Intermediate Similarity	NPC178382
0.838	Intermediate Similarity	NPC471292
0.8369	Intermediate Similarity	NPC199044
0.8369	Intermediate Similarity	NPC238843
0.8357	Intermediate Similarity	NPC20578
0.8357	Intermediate Similarity	NPC62103
0.8356	Intermediate Similarity	NPC34421
0.8356	Intermediate Similarity	NPC98206
0.8356	Intermediate Similarity	NPC253201
0.8356	Intermediate Similarity	NPC237259
0.8356	Intermediate Similarity	NPC30222
0.8356	Intermediate Similarity	NPC302054
0.8346	Intermediate Similarity	NPC87466
0.8346	Intermediate Similarity	NPC120836
0.8346	Intermediate Similarity	NPC223063
0.8345	Intermediate Similarity	NPC272590
0.8345	Intermediate Similarity	NPC148374
0.8333	Intermediate Similarity	NPC220094
0.8333	Intermediate Similarity	NPC476943
0.8322	Intermediate Similarity	NPC476938
0.8322	Intermediate Similarity	NPC476937
0.8321	Intermediate Similarity	NPC471074
0.8321	Intermediate Similarity	NPC473885
0.8311	Intermediate Similarity	NPC197137
0.8299	Intermediate Similarity	NPC214541
0.8299	Intermediate Similarity	NPC44675
0.8299	Intermediate Similarity	NPC296807
0.8299	Intermediate Similarity	NPC155939
0.8299	Intermediate Similarity	NPC141538
0.8298	Intermediate Similarity	NPC103134
0.8298	Intermediate Similarity	NPC223415
0.8295	Intermediate Similarity	NPC97566
0.8288	Intermediate Similarity	NPC246164
0.8288	Intermediate Similarity	NPC75906
0.8288	Intermediate Similarity	NPC121615
0.8288	Intermediate Similarity	NPC294511
0.8288	Intermediate Similarity	NPC268905
0.8276	Intermediate Similarity	NPC212257
0.8268	Intermediate Similarity	NPC208906
0.8268	Intermediate Similarity	NPC144745
0.8264	Intermediate Similarity	NPC93666
0.8261	Intermediate Similarity	NPC186626
0.8252	Intermediate Similarity	NPC470999
0.8244	Intermediate Similarity	NPC118853
0.8239	Intermediate Similarity	NPC158871
0.8235	Intermediate Similarity	NPC293253
0.8235	Intermediate Similarity	NPC470740
0.8231	Intermediate Similarity	NPC282445
0.8231	Intermediate Similarity	NPC36255
0.8231	Intermediate Similarity	NPC471549
0.8231	Intermediate Similarity	NPC44606
0.8231	Intermediate Similarity	NPC473379
0.8227	Intermediate Similarity	NPC473152
0.8214	Intermediate Similarity	NPC473983
0.8214	Intermediate Similarity	NPC201370
0.8214	Intermediate Similarity	NPC18904
0.8209	Intermediate Similarity	NPC208389
0.8195	Intermediate Similarity	NPC95567
0.8195	Intermediate Similarity	NPC319140
0.8194	Intermediate Similarity	NPC221809
0.8188	Intermediate Similarity	NPC472776
0.8188	Intermediate Similarity	NPC304692
0.8188	Intermediate Similarity	NPC475066
0.8188	Intermediate Similarity	NPC261597
0.8188	Intermediate Similarity	NPC194499
0.8188	Intermediate Similarity	NPC472777
0.8188	Intermediate Similarity	NPC470119
0.8188	Intermediate Similarity	NPC470118
0.8188	Intermediate Similarity	NPC472778
0.8188	Intermediate Similarity	NPC472772
0.8188	Intermediate Similarity	NPC214572
0.8188	Intermediate Similarity	NPC214495
0.8182	Intermediate Similarity	NPC41182
0.8182	Intermediate Similarity	NPC474829
0.8176	Intermediate Similarity	NPC264943
0.8175	Intermediate Similarity	NPC471998
0.8169	Intermediate Similarity	NPC470741
0.8169	Intermediate Similarity	NPC64568
0.8162	Intermediate Similarity	NPC471817
0.8156	Intermediate Similarity	NPC20500
0.8154	Intermediate Similarity	NPC79557
0.8151	Intermediate Similarity	NPC159927
0.8151	Intermediate Similarity	NPC228842
0.8151	Intermediate Similarity	NPC469335
0.8146	Intermediate Similarity	NPC69028
0.8146	Intermediate Similarity	NPC211777
0.8146	Intermediate Similarity	NPC5079
0.8143	Intermediate Similarity	NPC474722
0.8133	Intermediate Similarity	NPC474611
0.8133	Intermediate Similarity	NPC475967
0.8133	Intermediate Similarity	NPC472671
0.8133	Intermediate Similarity	NPC475226
0.8133	Intermediate Similarity	NPC307383
0.8129	Intermediate Similarity	NPC310043
0.8125	Intermediate Similarity	NPC262198
0.8121	Intermediate Similarity	NPC104736
0.8121	Intermediate Similarity	NPC41880
0.8112	Intermediate Similarity	NPC142113
0.8106	Intermediate Similarity	NPC83115
0.8099	Intermediate Similarity	NPC475519
0.8095	Intermediate Similarity	NPC116717
0.8092	Intermediate Similarity	NPC263870

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 NPC61788 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	912
0.2-0.3	1738
0.3-0.4	2621
0.4-0.5	2073
0.5-0.6	1214
0.6-0.7	327
0.7-0.8	17
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
0.8299	Intermediate Similarity	NPD5760	Phase 2
0.8299	Intermediate Similarity	NPD5761	Phase 2
0.7887	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6273	Approved
0.7531	Intermediate Similarity	NPD6764	Approved
0.7531	Intermediate Similarity	NPD6765	Approved
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.741	Intermediate Similarity	NPD8434	Phase 2
0.7349	Intermediate Similarity	NPD6785	Approved
0.7349	Intermediate Similarity	NPD6784	Approved
0.7279	Intermediate Similarity	NPD2344	Approved
0.7279	Intermediate Similarity	NPD1471	Phase 3
0.7273	Intermediate Similarity	NPD1241	Discontinued
0.726	Intermediate Similarity	NPD2799	Discontinued
0.7248	Intermediate Similarity	NPD7003	Approved
0.7246	Intermediate Similarity	NPD3972	Approved
0.7222	Intermediate Similarity	NPD4140	Approved
0.7208	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD1876	Approved
0.7086	Intermediate Similarity	NPD2309	Approved
0.7081	Intermediate Similarity	NPD8127	Discontinued
0.7063	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6355	Discontinued
0.705	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2798	Approved
0.7034	Intermediate Similarity	NPD8032	Phase 2
0.7029	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1283	Approved
0.702	Intermediate Similarity	NPD4110	Phase 3
0.702	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6559	Discontinued
0.698	Remote Similarity	NPD2935	Discontinued
0.6972	Remote Similarity	NPD2797	Approved
0.6966	Remote Similarity	NPD2313	Discontinued
0.6957	Remote Similarity	NPD5585	Approved
0.6954	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5327	Phase 3
0.6948	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5735	Approved
0.6933	Remote Similarity	NPD6002	Phase 3
0.6933	Remote Similarity	NPD6005	Phase 3
0.6933	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6004	Phase 3
0.6928	Remote Similarity	NPD7236	Approved
0.6906	Remote Similarity	NPD1778	Approved
0.6879	Remote Similarity	NPD7458	Discontinued
0.6879	Remote Similarity	NPD1608	Approved
0.6871	Remote Similarity	NPD2979	Phase 3
0.6867	Remote Similarity	NPD4477	Approved
0.6867	Remote Similarity	NPD2796	Approved
0.6867	Remote Similarity	NPD4476	Approved
0.6859	Remote Similarity	NPD920	Approved
0.6842	Remote Similarity	NPD2800	Approved
0.6839	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1651	Approved
0.6835	Remote Similarity	NPD5691	Approved
0.6828	Remote Similarity	NPD6832	Phase 2
0.6818	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7819	Suspended
0.6809	Remote Similarity	NPD1281	Approved
0.68	Remote Similarity	NPD4308	Phase 3
0.6797	Remote Similarity	NPD3750	Approved
0.6791	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7157	Approved
0.6786	Remote Similarity	NPD2932	Approved
0.6786	Remote Similarity	NPD4626	Approved
0.6781	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6353	Approved
0.6776	Remote Similarity	NPD2424	Discontinued
0.6772	Remote Similarity	NPD2649	Approved
0.6772	Remote Similarity	NPD2651	Approved
0.6772	Remote Similarity	NPD3226	Approved
0.6761	Remote Similarity	NPD9717	Approved
0.6759	Remote Similarity	NPD9494	Approved
0.6755	Remote Similarity	NPD6099	Approved
0.6755	Remote Similarity	NPD6100	Approved
0.6755	Remote Similarity	NPD1551	Phase 2
0.6738	Remote Similarity	NPD3496	Discontinued
0.6735	Remote Similarity	NPD6798	Discontinued
0.6735	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3268	Approved
0.6731	Remote Similarity	NPD2532	Approved
0.6731	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2534	Approved
0.6731	Remote Similarity	NPD2533	Approved
0.673	Remote Similarity	NPD7028	Phase 2
0.673	Remote Similarity	NPD6599	Discontinued
0.6726	Remote Similarity	NPD5844	Phase 1
0.6713	Remote Similarity	NPD4359	Approved
0.6711	Remote Similarity	NPD5763	Approved
0.6711	Remote Similarity	NPD5762	Approved
0.6711	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7239	Suspended
0.6708	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5494	Approved
0.669	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6663	Approved
0.6689	Remote Similarity	NPD3748	Approved
0.6688	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD4534	Discontinued
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD6696	Suspended
0.6667	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD6653	Approved
0.6647	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6279	Approved
0.6646	Remote Similarity	NPD6844	Discontinued
0.6646	Remote Similarity	NPD6280	Approved
0.6645	Remote Similarity	NPD2438	Suspended
0.6644	Remote Similarity	NPD4307	Phase 2
0.6644	Remote Similarity	NPD2861	Phase 2
0.6644	Remote Similarity	NPD4060	Phase 1
0.6644	Remote Similarity	NPD3142	Approved
0.6644	Remote Similarity	NPD3140	Approved
0.6644	Remote Similarity	NPD5736	Approved
0.6643	Remote Similarity	NPD1894	Discontinued
0.6642	Remote Similarity	NPD2684	Approved
0.6625	Remote Similarity	NPD4380	Phase 2
0.6624	Remote Similarity	NPD4662	Approved
0.6624	Remote Similarity	NPD4661	Approved
0.6623	Remote Similarity	NPD1243	Approved
0.6622	Remote Similarity	NPD3764	Approved
0.6622	Remote Similarity	NPD411	Approved
0.6622	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6362	Approved
0.6621	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1203	Approved
0.6605	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.66	Remote Similarity	NPD447	Suspended
0.6593	Remote Similarity	NPD3057	Approved
0.6577	Remote Similarity	NPD4870	Approved
0.6577	Remote Similarity	NPD6233	Phase 2
0.6575	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5647	Approved
0.6575	Remote Similarity	NPD1019	Discontinued
0.6575	Remote Similarity	NPD4624	Approved
0.6566	Remote Similarity	NPD6959	Discontinued
0.6566	Remote Similarity	NPD1247	Approved
0.6564	Remote Similarity	NPD2296	Approved
0.6558	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD5958	Discontinued
0.6556	Remote Similarity	NPD1607	Approved
0.6554	Remote Similarity	NPD7095	Approved
0.6554	Remote Similarity	NPD7008	Discontinued
0.6552	Remote Similarity	NPD8651	Approved
0.6547	Remote Similarity	NPD6671	Approved
0.6545	Remote Similarity	NPD919	Approved
0.6543	Remote Similarity	NPD37	Approved
0.6543	Remote Similarity	NPD1934	Approved
0.6541	Remote Similarity	NPD3869	Phase 3
0.6541	Remote Similarity	NPD3873	Phase 3
0.6536	Remote Similarity	NPD2531	Phase 2
0.6533	Remote Similarity	NPD3620	Phase 2
0.6533	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1240	Approved
0.6525	Remote Similarity	NPD9545	Approved
0.6524	Remote Similarity	NPD4967	Phase 2
0.6524	Remote Similarity	NPD7768	Phase 2
0.6524	Remote Similarity	NPD3882	Suspended
0.6524	Remote Similarity	NPD4965	Approved
0.6524	Remote Similarity	NPD4966	Approved
0.6513	Remote Similarity	NPD7097	Phase 1
0.651	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD3267	Approved
0.6507	Remote Similarity	NPD3266	Approved
0.6503	Remote Similarity	NPD2491	Approved
0.6503	Remote Similarity	NPD2972	Approved
0.6503	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3533	Approved
0.6497	Remote Similarity	NPD7440	Discontinued
0.6496	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD3134	Approved
0.649	Remote Similarity	NPD4618	Approved
0.649	Remote Similarity	NPD4622	Approved
0.6486	Remote Similarity	NPD2614	Approved
0.6485	Remote Similarity	NPD3749	Approved
0.6485	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7075	Discontinued
0.6481	Remote Similarity	NPD7411	Suspended
0.6479	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD2629	Approved
0.6471	Remote Similarity	NPD7033	Discontinued
0.6471	Remote Similarity	NPD3818	Discontinued
0.6471	Remote Similarity	NPD1510	Phase 2
0.6471	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4062	Phase 3
0.6456	Remote Similarity	NPD6799	Approved
0.6449	Remote Similarity	NPD7843	Approved
0.6447	Remote Similarity	NPD2157	Approved
0.6444	Remote Similarity	NPD290	Approved
0.6442	Remote Similarity	NPD6801	Discontinued
0.6442	Remote Similarity	NPD7577	Discontinued

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