NPASS Compound

Structure

NPC307401 OpenBabel07101719242D 24 27 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 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 0.5000 -0.8660 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 -1.7321 -2.0000 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 -5.2812 -1.8090 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -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 1 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 14 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 7 19 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 23 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 1 1 1 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 22 2 0 0 0 0 14 24 1 0 0 0 0 15 6 1 1 0 0 0 15 17 1 0 0 0 0 16 18 2 0 0 0 0 17 20 1 6 0 0 0 18 23 1 0 0 0 0 19 20 1 6 0 0 0 19 21 1 0 0 0 0 20 3 1 6 0 0 0 21 4 1 1 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.22
Volume:	356.008
LogP:	4.911
LogD:	4.524
LogS:	-4.993
# Rotatable Bonds:	2
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	4.512
Fsp3:	0.762
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:	-4.719
MDCK Permeability:	2.2752166842110455e-05
Pgp-inhibitor:	0.951
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.387
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	95.18695068359375%
Volume Distribution (VD):	2.411
Pgp-substrate:	3.550715446472168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.625
CYP1A2-substrate:	0.358
CYP2C19-inhibitor:	0.414
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.391
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.313
CYP2D6-substrate:	0.211
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.667

ADMET: Excretion

Clearance (CL):	6.811
Half-life (T1/2):	0.207

ADMET: Toxicity

hERG Blockers:	0.813
Human Hepatotoxicity (H-HT):	0.511
Drug-inuced Liver Injury (DILI):	0.858
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.149
Skin Sensitization:	0.636
Carcinogencity:	0.203
Eye Corrosion:	0.016
Eye Irritation:	0.055
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC307401

Natural Product ID:	NPC307401
*Common Name:**	Deoxycaesaldekarin C
IUPAC Name:	[(4S,4aR,6aS,7R,11aS,11bR)-4,7,11b-trimethyl-1,2,3,4a,5,6,6a,7,11,11a-decahydronaphtho[2,1-f][1]benzofuran-4-yl] acetate
Synonyms:
Standard InCHIKey:	YUAQBFTWNHXSHR-MEOKCCQFSA-N
Standard InCHI:	InChI=1S/C21H30O3/c1-13-15-6-7-19-20(3,9-5-10-21(19,4)24-14(2)22)17(15)12-18-16(13)8-11-23-18/h8,11,13,15,17,19H,5-7,9-10,12H2,1-4H3/t13-,15+,17+,19-,20-,21+/m1/s1
SMILES:	C[C@@H]1[C@@H]2CC[C@@H]3[C@](C)(CCC[C@]3(C)OC(=O)C)[C@H]2Cc2c1cco2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2381691
PubChem CID:	73354919
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO33322	caesalpinia volkensii	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[23562058]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	30330.0	nM	PMID[548783]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	25670.0	nM	PMID[548783]

☑ 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 NPC307401 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	332
0.1-0.2	1443
0.2-0.3	2553
0.3-0.4	6308
0.4-0.5	11409
0.5-0.6	8088
0.6-0.7	10278
0.7-0.8	1975
0.8-0.85	223
0.85-0.9	72
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC202260
0.9231	High Similarity	NPC59502
0.9197	High Similarity	NPC263337
0.9143	High Similarity	NPC71821
0.9137	High Similarity	NPC290038
0.9098	High Similarity	NPC293253
0.9085	High Similarity	NPC228842
0.9085	High Similarity	NPC212257
0.9071	High Similarity	NPC233763
0.8992	High Similarity	NPC178382
0.8915	High Similarity	NPC16922
0.8881	High Similarity	NPC95526
0.8865	High Similarity	NPC56731
0.8855	High Similarity	NPC74612
0.8828	High Similarity	NPC294511
0.8828	High Similarity	NPC121615
0.8819	High Similarity	NPC472298
0.8797	High Similarity	NPC198904
0.8779	High Similarity	NPC179354
0.8777	High Similarity	NPC56197
0.8776	High Similarity	NPC104736
0.8776	High Similarity	NPC41880
0.876	High Similarity	NPC97566
0.8716	High Similarity	NPC195954
0.8716	High Similarity	NPC88007
0.8716	High Similarity	NPC7059
0.8716	High Similarity	NPC304692
0.8716	High Similarity	NPC194499
0.8712	High Similarity	NPC138139
0.8712	High Similarity	NPC46536
0.8707	High Similarity	NPC25351
0.8705	High Similarity	NPC474722
0.8692	High Similarity	NPC36255
0.8681	High Similarity	NPC93666
0.8667	High Similarity	NPC298190
0.8657	High Similarity	NPC208389
0.8643	High Similarity	NPC148374
0.8639	High Similarity	NPC44606
0.8636	High Similarity	NPC471074
0.8636	High Similarity	NPC473885
0.86	High Similarity	NPC8389
0.86	High Similarity	NPC287559
0.8591	High Similarity	NPC81405
0.8582	High Similarity	NPC112706
0.8582	High Similarity	NPC207294
0.8582	High Similarity	NPC476917
0.8582	High Similarity	NPC327527
0.8561	High Similarity	NPC170604
0.8561	High Similarity	NPC215109
0.8561	High Similarity	NPC83115
0.8561	High Similarity	NPC130275
0.8552	High Similarity	NPC19747
0.8551	High Similarity	NPC476947
0.8543	High Similarity	NPC68848
0.8543	High Similarity	NPC18986
0.8543	High Similarity	NPC79571
0.8542	High Similarity	NPC478166
0.8542	High Similarity	NPC62799
0.8533	High Similarity	NPC474611
0.8533	High Similarity	NPC140952
0.8531	High Similarity	NPC238843
0.8531	High Similarity	NPC199044
0.8529	High Similarity	NPC61788
0.8521	High Similarity	NPC121158
0.8507	High Similarity	NPC83178
0.8503	High Similarity	NPC144010
0.85	High Similarity	NPC476943
0.8496	Intermediate Similarity	NPC230979
0.8493	Intermediate Similarity	NPC211625
0.8489	Intermediate Similarity	NPC46896
0.8487	Intermediate Similarity	NPC285567
0.8487	Intermediate Similarity	NPC475039
0.8487	Intermediate Similarity	NPC283209
0.8487	Intermediate Similarity	NPC476035
0.8487	Intermediate Similarity	NPC14499
0.8483	Intermediate Similarity	NPC224418
0.8483	Intermediate Similarity	NPC216755
0.8472	Intermediate Similarity	NPC114513
0.8472	Intermediate Similarity	NPC245522
0.8467	Intermediate Similarity	NPC473982
0.8462	Intermediate Similarity	NPC470273
0.8456	Intermediate Similarity	NPC476925
0.845	Intermediate Similarity	NPC212918
0.8446	Intermediate Similarity	NPC246164
0.8444	Intermediate Similarity	NPC329707
0.8444	Intermediate Similarity	NPC279877
0.844	Intermediate Similarity	NPC233707
0.8429	Intermediate Similarity	NPC42400
0.8421	Intermediate Similarity	NPC188377
0.8421	Intermediate Similarity	NPC188649
0.8421	Intermediate Similarity	NPC471003
0.8421	Intermediate Similarity	NPC65735
0.8421	Intermediate Similarity	NPC118853
0.8417	Intermediate Similarity	NPC324117
0.8417	Intermediate Similarity	NPC209858
0.8414	Intermediate Similarity	NPC471292
0.8411	Intermediate Similarity	NPC123153
0.8406	Intermediate Similarity	NPC218838
0.8406	Intermediate Similarity	NPC470740
0.8403	Intermediate Similarity	NPC251865
0.8403	Intermediate Similarity	NPC84479
0.8394	Intermediate Similarity	NPC89133
0.8389	Intermediate Similarity	NPC10429
0.8385	Intermediate Similarity	NPC87466
0.8385	Intermediate Similarity	NPC243704
0.8377	Intermediate Similarity	NPC277618
0.8377	Intermediate Similarity	NPC121995
0.8372	Intermediate Similarity	NPC59035
0.8372	Intermediate Similarity	NPC79202
0.837	Intermediate Similarity	NPC290955
0.837	Intermediate Similarity	NPC246392
0.8369	Intermediate Similarity	NPC236532
0.8366	Intermediate Similarity	NPC88841
0.8366	Intermediate Similarity	NPC288602
0.8358	Intermediate Similarity	NPC290193
0.8357	Intermediate Similarity	NPC214572
0.8357	Intermediate Similarity	NPC146872
0.8356	Intermediate Similarity	NPC471174
0.8356	Intermediate Similarity	NPC281398
0.8355	Intermediate Similarity	NPC472299
0.8333	Intermediate Similarity	NPC205071
0.8312	Intermediate Similarity	NPC276735
0.8312	Intermediate Similarity	NPC56358
0.8311	Intermediate Similarity	NPC477404
0.8311	Intermediate Similarity	NPC196864
0.8309	Intermediate Similarity	NPC477040
0.8309	Intermediate Similarity	NPC26532
0.8298	Intermediate Similarity	NPC470742
0.8298	Intermediate Similarity	NPC310830
0.8298	Intermediate Similarity	NPC310043
0.8296	Intermediate Similarity	NPC23086
0.8295	Intermediate Similarity	NPC150895
0.8289	Intermediate Similarity	NPC472823
0.8288	Intermediate Similarity	NPC262198
0.8286	Intermediate Similarity	NPC158525
0.8276	Intermediate Similarity	NPC476944
0.8273	Intermediate Similarity	NPC471006
0.8269	Intermediate Similarity	NPC296558
0.8267	Intermediate Similarity	NPC471863
0.8267	Intermediate Similarity	NPC114880
0.8264	Intermediate Similarity	NPC52412
0.8252	Intermediate Similarity	NPC476191
0.8252	Intermediate Similarity	NPC67003
0.8248	Intermediate Similarity	NPC120836
0.8248	Intermediate Similarity	NPC223063
0.8243	Intermediate Similarity	NPC234494
0.8243	Intermediate Similarity	NPC471001
0.8239	Intermediate Similarity	NPC177262
0.8239	Intermediate Similarity	NPC220094
0.8231	Intermediate Similarity	NPC286038
0.8231	Intermediate Similarity	NPC255414
0.8231	Intermediate Similarity	NPC221809
0.8222	Intermediate Similarity	NPC300098
0.8217	Intermediate Similarity	NPC302392
0.8217	Intermediate Similarity	NPC88593
0.8209	Intermediate Similarity	NPC272899
0.8207	Intermediate Similarity	NPC243577
0.8205	Intermediate Similarity	NPC473766
0.8205	Intermediate Similarity	NPC41689
0.8205	Intermediate Similarity	NPC473753
0.8205	Intermediate Similarity	NPC270312
0.8201	Intermediate Similarity	NPC164295
0.8201	Intermediate Similarity	NPC196979
0.8201	Intermediate Similarity	NPC470976
0.8201	Intermediate Similarity	NPC470977
0.8201	Intermediate Similarity	NPC471817
0.8194	Intermediate Similarity	NPC126984
0.8194	Intermediate Similarity	NPC27541
0.8194	Intermediate Similarity	NPC62692
0.8194	Intermediate Similarity	NPC61967
0.8188	Intermediate Similarity	NPC469335
0.8188	Intermediate Similarity	NPC470997
0.8188	Intermediate Similarity	NPC159927
0.8188	Intermediate Similarity	NPC476122
0.8188	Intermediate Similarity	NPC156189
0.8176	Intermediate Similarity	NPC66991
0.8175	Intermediate Similarity	NPC477966
0.8175	Intermediate Similarity	NPC477123
0.817	Intermediate Similarity	NPC473368
0.817	Intermediate Similarity	NPC84349
0.8168	Intermediate Similarity	NPC227660
0.8163	Intermediate Similarity	NPC346
0.8158	Intermediate Similarity	NPC107646
0.8156	Intermediate Similarity	NPC92941
0.8154	Intermediate Similarity	NPC205523
0.8151	Intermediate Similarity	NPC142113
0.8148	Intermediate Similarity	NPC243269
0.8141	Intermediate Similarity	NPC308156
0.8133	Intermediate Similarity	NPC272590
0.8129	Intermediate Similarity	NPC282230
0.8129	Intermediate Similarity	NPC183348
0.8121	Intermediate Similarity	NPC470790
0.8121	Intermediate Similarity	NPC470791
0.8121	Intermediate Similarity	NPC69647
0.8121	Intermediate Similarity	NPC125182
0.8121	Intermediate Similarity	NPC192069
0.8108	Intermediate Similarity	NPC470941
0.8095	Intermediate Similarity	NPC27798
0.8095	Intermediate Similarity	NPC185456
0.8095	Intermediate Similarity	NPC93241

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 NPC307401 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	942
0.2-0.3	1297
0.3-0.4	2462
0.4-0.5	2244
0.5-0.6	1362
0.6-0.7	461
0.7-0.8	77
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
0.831	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD6273	Approved
0.8201	Intermediate Similarity	NPD8032	Phase 2
0.7922	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD7003	Approved
0.781	Intermediate Similarity	NPD3972	Approved
0.7808	Intermediate Similarity	NPD1471	Phase 3
0.7793	Intermediate Similarity	NPD2799	Discontinued
0.7791	Intermediate Similarity	NPD6764	Approved
0.7791	Intermediate Similarity	NPD6765	Approved
0.7742	Intermediate Similarity	NPD5761	Phase 2
0.7742	Intermediate Similarity	NPD5760	Phase 2
0.7703	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD1876	Approved
0.7687	Intermediate Similarity	NPD2346	Discontinued
0.7665	Intermediate Similarity	NPD8434	Phase 2
0.7651	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD5585	Approved
0.7639	Intermediate Similarity	NPD4140	Approved
0.7639	Intermediate Similarity	NPD4307	Phase 2
0.7609	Intermediate Similarity	NPD1281	Approved
0.7609	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6832	Phase 2
0.7605	Intermediate Similarity	NPD6784	Approved
0.7605	Intermediate Similarity	NPD6785	Approved
0.7597	Intermediate Similarity	NPD7458	Discontinued
0.7597	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1241	Discontinued
0.7591	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD2798	Approved
0.7551	Intermediate Similarity	NPD3748	Approved
0.755	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD5691	Approved
0.7518	Intermediate Similarity	NPD2797	Approved
0.7518	Intermediate Similarity	NPD3267	Approved
0.7518	Intermediate Similarity	NPD3266	Approved
0.7517	Intermediate Similarity	NPD2979	Phase 3
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD5327	Phase 3
0.7468	Intermediate Similarity	NPD920	Approved
0.7464	Intermediate Similarity	NPD17	Approved
0.7451	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2344	Approved
0.7447	Intermediate Similarity	NPD1283	Approved
0.7432	Intermediate Similarity	NPD4308	Phase 3
0.7431	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7819	Suspended
0.7391	Intermediate Similarity	NPD1651	Approved
0.7383	Intermediate Similarity	NPD2796	Approved
0.7379	Intermediate Similarity	NPD3268	Approved
0.7379	Intermediate Similarity	NPD3764	Approved
0.7376	Intermediate Similarity	NPD4359	Approved
0.7372	Intermediate Similarity	NPD3226	Approved
0.7368	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1243	Approved
0.7347	Intermediate Similarity	NPD6355	Discontinued
0.7347	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD8127	Discontinued
0.7338	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6599	Discontinued
0.732	Intermediate Similarity	NPD7236	Approved
0.731	Intermediate Similarity	NPD7095	Approved
0.7305	Intermediate Similarity	NPD1608	Approved
0.7303	Intermediate Similarity	NPD4110	Phase 3
0.7303	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3750	Approved
0.7303	Intermediate Similarity	NPD8166	Discontinued
0.7267	Intermediate Similarity	NPD3749	Approved
0.7267	Intermediate Similarity	NPD2531	Phase 2
0.7267	Intermediate Similarity	NPD2438	Suspended
0.7267	Intermediate Similarity	NPD4477	Approved
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7267	Intermediate Similarity	NPD4476	Approved
0.726	Intermediate Similarity	NPD6798	Discontinued
0.7259	Intermediate Similarity	NPD5535	Approved
0.7255	Intermediate Similarity	NPD2309	Approved
0.7255	Intermediate Similarity	NPD3887	Approved
0.723	Intermediate Similarity	NPD4622	Approved
0.723	Intermediate Similarity	NPD4618	Approved
0.7222	Intermediate Similarity	NPD919	Approved
0.7214	Intermediate Similarity	NPD4626	Approved
0.7214	Intermediate Similarity	NPD1778	Approved
0.7211	Intermediate Similarity	NPD6663	Approved
0.7197	Intermediate Similarity	NPD3134	Approved
0.7172	Intermediate Similarity	NPD5736	Approved
0.717	Intermediate Similarity	NPD7411	Suspended
0.7163	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6559	Discontinued
0.7152	Intermediate Similarity	NPD6100	Approved
0.7152	Intermediate Similarity	NPD6099	Approved
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD3024	Approved
0.7143	Intermediate Similarity	NPD3025	Approved
0.7134	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5688	Approved
0.7133	Intermediate Similarity	NPD5689	Approved
0.7126	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6279	Approved
0.7125	Intermediate Similarity	NPD6280	Approved
0.7114	Intermediate Similarity	NPD1933	Approved
0.7107	Intermediate Similarity	NPD7028	Phase 2
0.7105	Intermediate Similarity	NPD2353	Approved
0.7105	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1019	Discontinued
0.7099	Intermediate Similarity	NPD7768	Phase 2
0.7095	Intermediate Similarity	NPD4870	Approved
0.7092	Intermediate Similarity	NPD3019	Approved
0.7091	Intermediate Similarity	NPD6808	Phase 2
0.7089	Intermediate Similarity	NPD7239	Suspended
0.7081	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7008	Discontinued
0.7073	Intermediate Similarity	NPD5494	Approved
0.7071	Intermediate Similarity	NPD1894	Discontinued
0.7067	Intermediate Similarity	NPD6353	Approved
0.7063	Intermediate Similarity	NPD9717	Approved
0.7059	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2897	Discontinued
0.7051	Intermediate Similarity	NPD6799	Approved
0.7047	Intermediate Similarity	NPD3142	Approved
0.7047	Intermediate Similarity	NPD4060	Phase 1
0.7047	Intermediate Similarity	NPD3140	Approved
0.7042	Intermediate Similarity	NPD3496	Discontinued
0.7042	Intermediate Similarity	NPD3023	Approved
0.7042	Intermediate Similarity	NPD3026	Approved
0.7034	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1203	Approved
0.7029	Intermediate Similarity	NPD5951	Approved
0.7025	Intermediate Similarity	NPD3869	Phase 3
0.7025	Intermediate Similarity	NPD7427	Discontinued
0.7025	Intermediate Similarity	NPD3873	Phase 3
0.702	Intermediate Similarity	NPD7097	Phase 1
0.7	Intermediate Similarity	NPD5735	Approved
0.6993	Remote Similarity	NPD6287	Discontinued
0.6993	Remote Similarity	NPD1611	Approved
0.6987	Remote Similarity	NPD7440	Discontinued
0.6986	Remote Similarity	NPD4624	Approved
0.6982	Remote Similarity	NPD5844	Phase 1
0.698	Remote Similarity	NPD6233	Phase 2
0.6972	Remote Similarity	NPD2932	Approved
0.6963	Remote Similarity	NPD2182	Approved
0.6962	Remote Similarity	NPD5049	Phase 3
0.6957	Remote Similarity	NPD6873	Phase 2
0.6951	Remote Similarity	NPD7075	Discontinued
0.6948	Remote Similarity	NPD4534	Discontinued
0.6943	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7177	Discontinued
0.6923	Remote Similarity	NPD2354	Approved
0.6914	Remote Similarity	NPD7577	Discontinued
0.6914	Remote Similarity	NPD6801	Discontinued
0.6913	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD411	Approved
0.6905	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2532	Approved
0.6899	Remote Similarity	NPD2534	Approved
0.6899	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2533	Approved
0.6892	Remote Similarity	NPD2614	Approved
0.689	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1358	Approved
0.6884	Remote Similarity	NPD6858	Approved
0.6884	Remote Similarity	NPD7094	Approved
0.6883	Remote Similarity	NPD6005	Phase 3
0.6883	Remote Similarity	NPD6002	Phase 3
0.6883	Remote Similarity	NPD5762	Approved
0.6883	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6004	Phase 3
0.6883	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5763	Approved
0.687	Remote Similarity	NPD1238	Approved
0.6866	Remote Similarity	NPD9697	Approved
0.6863	Remote Similarity	NPD7033	Discontinued
0.6852	Remote Similarity	NPD6677	Suspended
0.6852	Remote Similarity	NPD5889	Approved
0.6852	Remote Similarity	NPD5890	Approved
0.6839	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5958	Discontinued
0.6839	Remote Similarity	NPD1549	Phase 2
0.6832	Remote Similarity	NPD2649	Approved
0.6832	Remote Similarity	NPD2651	Approved
0.6831	Remote Similarity	NPD9545	Approved
0.6829	Remote Similarity	NPD3817	Phase 2
0.6826	Remote Similarity	NPD1247	Approved
0.6813	Remote Similarity	NPD4107	Approved
0.6813	Remote Similarity	NPD5403	Approved
0.681	Remote Similarity	NPD37	Approved
0.68	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5401	Approved
0.679	Remote Similarity	NPD6585	Discontinued
0.6788	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4965	Approved
0.6788	Remote Similarity	NPD7057	Phase 3
0.6788	Remote Similarity	NPD7058	Phase 2
0.6788	Remote Similarity	NPD4967	Phase 2
0.6788	Remote Similarity	NPD4966	Approved
0.6786	Remote Similarity	NPD7229	Phase 3
0.6782	Remote Similarity	NPD8313	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