NPASS Compound

Structure

CID214572 OpenBabel06191716002D 30 34 0 0 1 0 0 0 0 0999 V2000 -1.8841 -2.9013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -0.6340 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 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 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 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 -0.1615 -3.0823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 22 1 0 0 0 0 14 23 1 0 0 0 0 15 18 2 0 0 0 0 15 29 1 0 0 0 0 16 19 2 0 0 0 0 16 29 1 0 0 0 0 17 28 2 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 19 27 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 1 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 25 1 1 0 0 0 22 26 1 0 0 0 0 23 27 1 6 0 0 0 23 30 1 0 0 0 0 25 4 1 1 0 0 0 26 5 1 1 0 0 0 27 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.3
Volume:	451.227
LogP:	6.318
LogD:	5.151
LogS:	-6.205
# Rotatable Bonds:	2
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.483
Synthetic Accessibility Score:	4.656
Fsp3:	0.815
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.829
MDCK Permeability:	1.534913099021651e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.238
Plasma Protein Binding (PPB):	92.94388580322266%
Volume Distribution (VD):	1.944
Pgp-substrate:	3.947113513946533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.551
CYP2C9-inhibitor:	0.282
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.509
CYP2D6-substrate:	0.834
CYP3A4-inhibitor:	0.616
CYP3A4-substrate:	0.395

ADMET: Excretion

Clearance (CL):	9.79
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.489
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.386
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.974
Maximum Recommended Daily Dose:	0.859
Skin Sensitization:	0.472
Carcinogencity:	0.655
Eye Corrosion:	0.139
Eye Irritation:	0.167
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC214572

Natural Product ID:	NPC214572
*Common Name:**	16-Deacetyl-12-Epi-Scalarafuran Acetate
IUPAC Name:	[(5aS,5bR,7aS,11aS,11bR,13S,13aS)-5b,8,8,11a,13a-pentamethyl-4,5,5a,6,7,7a,9,10,11,11b,12,13-dodecahydrophenanthro[2,1-e][2]benzofuran-13-yl] acetate
Synonyms:
Standard InCHIKey:	WAADVUIWRUHATI-NXQORITBSA-N
Standard InCHI:	InChI=1S/C27H40O3/c1-17(28)30-23-14-22-25(4)12-7-11-24(2,3)20(25)10-13-26(22,5)21-9-8-18-15-29-16-19(18)27(21,23)6/h15-16,20-23H,7-14H2,1-6H3/t20-,21-,22+,23-,25-,26-,27+/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@@H]2[C@@]3(C)CCCC([C@@H]3CC[C@]2([C@H]2[C@@]1(C)c1cocc1CC2)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521172
PubChem CID:	15625488
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548580]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31095383]
NPO6350	Spongia officinalis	Species	Spongiidae	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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	180.0	ug ml-1	PMID[506897]

☑ 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 NPC214572 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	338
0.1-0.2	1456
0.2-0.3	3179
0.3-0.4	6005
0.4-0.5	10830
0.5-0.6	11893
0.6-0.7	7933
0.7-0.8	776
0.8-0.85	234
0.85-0.9	45
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC310043
0.947	High Similarity	NPC4764
0.9343	High Similarity	NPC41182
0.9154	High Similarity	NPC198904
0.9124	High Similarity	NPC62103
0.9124	High Similarity	NPC20578
0.9062	High Similarity	NPC83115
0.8992	High Similarity	NPC230979
0.8921	High Similarity	NPC103134
0.8906	High Similarity	NPC36255
0.8849	High Similarity	NPC121158
0.875	High Similarity	NPC159927
0.875	High Similarity	NPC196864
0.875	High Similarity	NPC469335
0.875	High Similarity	NPC477404
0.875	High Similarity	NPC476122
0.8723	High Similarity	NPC251865
0.8722	High Similarity	NPC120836
0.8722	High Similarity	NPC223063
0.8671	High Similarity	NPC216755
0.8671	High Similarity	NPC71821
0.8652	High Similarity	NPC205071
0.863	High Similarity	NPC476201
0.863	High Similarity	NPC469503
0.8626	High Similarity	NPC130275
0.8603	High Similarity	NPC293253
0.8601	High Similarity	NPC62799
0.8591	High Similarity	NPC474611
0.8581	High Similarity	NPC107646
0.8571	High Similarity	NPC56197
0.8571	High Similarity	NPC178932
0.8571	High Similarity	NPC282445
0.8571	High Similarity	NPC30222
0.8571	High Similarity	NPC67003
0.8561	High Similarity	NPC303010
0.8561	High Similarity	NPC471996
0.8552	High Similarity	NPC471001
0.8552	High Similarity	NPC472654
0.8542	High Similarity	NPC471174
0.8542	High Similarity	NPC221809
0.8542	High Similarity	NPC470941
0.8542	High Similarity	NPC255414
0.8516	High Similarity	NPC212918
0.8514	High Similarity	NPC476262
0.8514	High Similarity	NPC469336
0.8514	High Similarity	NPC35000
0.8514	High Similarity	NPC469850
0.8493	Intermediate Similarity	NPC156189
0.8493	Intermediate Similarity	NPC212257
0.8483	Intermediate Similarity	NPC19747
0.8472	Intermediate Similarity	NPC471292
0.8462	Intermediate Similarity	NPC199044
0.8462	Intermediate Similarity	NPC238843
0.8456	Intermediate Similarity	NPC41880
0.8456	Intermediate Similarity	NPC209364
0.8435	Intermediate Similarity	NPC18135
0.8429	Intermediate Similarity	NPC476943
0.8425	Intermediate Similarity	NPC470790
0.8425	Intermediate Similarity	NPC211625
0.8425	Intermediate Similarity	NPC125182
0.8425	Intermediate Similarity	NPC69647
0.8425	Intermediate Similarity	NPC195325
0.8425	Intermediate Similarity	NPC470791
0.8411	Intermediate Similarity	NPC475381
0.8411	Intermediate Similarity	NPC335761
0.8409	Intermediate Similarity	NPC272899
0.8406	Intermediate Similarity	NPC471998
0.84	Intermediate Similarity	NPC286722
0.84	Intermediate Similarity	NPC472283
0.84	Intermediate Similarity	NPC7059
0.84	Intermediate Similarity	NPC249021
0.8394	Intermediate Similarity	NPC471995
0.8392	Intermediate Similarity	NPC223415
0.8389	Intermediate Similarity	NPC92979
0.8378	Intermediate Similarity	NPC294511
0.8378	Intermediate Similarity	NPC246164
0.8378	Intermediate Similarity	NPC121615
0.8358	Intermediate Similarity	NPC74612
0.8357	Intermediate Similarity	NPC307401
0.8357	Intermediate Similarity	NPC310830
0.8355	Intermediate Similarity	NPC470939
0.8345	Intermediate Similarity	NPC470999
0.8344	Intermediate Similarity	NPC473473
0.8344	Intermediate Similarity	NPC307383
0.8344	Intermediate Similarity	NPC475295
0.8333	Intermediate Similarity	NPC126723
0.8333	Intermediate Similarity	NPC142113
0.8333	Intermediate Similarity	NPC84479
0.8333	Intermediate Similarity	NPC104736
0.8333	Intermediate Similarity	NPC476944
0.8322	Intermediate Similarity	NPC263337
0.8321	Intermediate Similarity	NPC298190
0.8311	Intermediate Similarity	NPC116717
0.8311	Intermediate Similarity	NPC272590
0.8301	Intermediate Similarity	NPC134254
0.8301	Intermediate Similarity	NPC39986
0.8301	Intermediate Similarity	NPC476197
0.8301	Intermediate Similarity	NPC302369
0.8301	Intermediate Similarity	NPC469846
0.8289	Intermediate Similarity	NPC8389
0.8286	Intermediate Similarity	NPC46896
0.8284	Intermediate Similarity	NPC179354
0.8278	Intermediate Similarity	NPC194499
0.8278	Intermediate Similarity	NPC88007
0.8278	Intermediate Similarity	NPC469847
0.8278	Intermediate Similarity	NPC195954
0.8278	Intermediate Similarity	NPC167142
0.8278	Intermediate Similarity	NPC304692
0.8278	Intermediate Similarity	NPC472772
0.8276	Intermediate Similarity	NPC5676
0.8271	Intermediate Similarity	NPC16922
0.8267	Intermediate Similarity	NPC141538
0.8267	Intermediate Similarity	NPC296807
0.8267	Intermediate Similarity	NPC155939
0.8264	Intermediate Similarity	NPC470741
0.8264	Intermediate Similarity	NPC243577
0.8264	Intermediate Similarity	NPC64568
0.8255	Intermediate Similarity	NPC472672
0.8255	Intermediate Similarity	NPC308205
0.8255	Intermediate Similarity	NPC322546
0.8255	Intermediate Similarity	NPC182427
0.8255	Intermediate Similarity	NPC268905
0.8255	Intermediate Similarity	NPC29695
0.8255	Intermediate Similarity	NPC475777
0.8255	Intermediate Similarity	NPC471002
0.8252	Intermediate Similarity	NPC20500
0.8243	Intermediate Similarity	NPC470997
0.8243	Intermediate Similarity	NPC228842
0.8239	Intermediate Similarity	NPC202260
0.8239	Intermediate Similarity	NPC90953
0.8235	Intermediate Similarity	NPC68848
0.8235	Intermediate Similarity	NPC82851
0.8235	Intermediate Similarity	NPC471003
0.8235	Intermediate Similarity	NPC470792
0.8235	Intermediate Similarity	NPC79571
0.8235	Intermediate Similarity	NPC200782
0.8235	Intermediate Similarity	NPC5079
0.8235	Intermediate Similarity	NPC69028
0.8219	Intermediate Similarity	NPC262198
0.8212	Intermediate Similarity	NPC60973
0.8209	Intermediate Similarity	NPC178382
0.8205	Intermediate Similarity	NPC296558
0.82	Intermediate Similarity	NPC253201
0.82	Intermediate Similarity	NPC302054
0.82	Intermediate Similarity	NPC57998
0.82	Intermediate Similarity	NPC237259
0.82	Intermediate Similarity	NPC34421
0.82	Intermediate Similarity	NPC114880
0.82	Intermediate Similarity	NPC98206
0.8188	Intermediate Similarity	NPC291150
0.8188	Intermediate Similarity	NPC471000
0.8188	Intermediate Similarity	NPC89133
0.8188	Intermediate Similarity	NPC61788
0.8182	Intermediate Similarity	NPC234660
0.8182	Intermediate Similarity	NPC292389
0.8182	Intermediate Similarity	NPC51568
0.8182	Intermediate Similarity	NPC469338
0.8182	Intermediate Similarity	NPC477405
0.8176	Intermediate Similarity	NPC234494
0.817	Intermediate Similarity	NPC287559
0.817	Intermediate Similarity	NPC472653
0.8169	Intermediate Similarity	NPC220094
0.8163	Intermediate Similarity	NPC250228
0.8158	Intermediate Similarity	NPC299038
0.8146	Intermediate Similarity	NPC44675
0.8146	Intermediate Similarity	NPC264943
0.8146	Intermediate Similarity	NPC214541
0.8146	Intermediate Similarity	NPC75310
0.8146	Intermediate Similarity	NPC25351
0.8141	Intermediate Similarity	NPC472282
0.8133	Intermediate Similarity	NPC75906
0.8133	Intermediate Similarity	NPC33938
0.8129	Intermediate Similarity	NPC470182
0.8129	Intermediate Similarity	NPC469849
0.8129	Intermediate Similarity	NPC276551
0.8129	Intermediate Similarity	NPC470940
0.8121	Intermediate Similarity	NPC5180
0.8117	Intermediate Similarity	NPC472771
0.8117	Intermediate Similarity	NPC188649
0.8117	Intermediate Similarity	NPC211777
0.8117	Intermediate Similarity	NPC207978
0.8117	Intermediate Similarity	NPC197596
0.8117	Intermediate Similarity	NPC263432
0.8117	Intermediate Similarity	NPC329938
0.8108	Intermediate Similarity	NPC471007
0.8105	Intermediate Similarity	NPC474932
0.8105	Intermediate Similarity	NPC475967
0.8105	Intermediate Similarity	NPC475226
0.8105	Intermediate Similarity	NPC237155
0.8102	Intermediate Similarity	NPC327527
0.8102	Intermediate Similarity	NPC476917
0.8099	Intermediate Similarity	NPC470742
0.8095	Intermediate Similarity	NPC346
0.8095	Intermediate Similarity	NPC233763
0.8095	Intermediate Similarity	NPC97904
0.8092	Intermediate Similarity	NPC263265
0.8089	Intermediate Similarity	NPC160651
0.8089	Intermediate Similarity	NPC271235
0.8088	Intermediate Similarity	NPC46536
0.8088	Intermediate Similarity	NPC138139

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 NPC214572 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	1053
0.2-0.3	2062
0.3-0.4	2732
0.4-0.5	1957
0.5-0.6	827
0.6-0.7	210
0.7-0.8	7
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
0.8146	Intermediate Similarity	NPD5760	Phase 2
0.8146	Intermediate Similarity	NPD5761	Phase 2
0.7707	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6273	Approved
0.7396	Intermediate Similarity	NPD8434	Phase 2
0.7383	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4628	Phase 3
0.7202	Intermediate Similarity	NPD6765	Approved
0.7202	Intermediate Similarity	NPD6764	Approved
0.7161	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8032	Phase 2
0.7073	Intermediate Similarity	NPD8127	Discontinued
0.707	Intermediate Similarity	NPD920	Approved
0.7059	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2532	Approved
0.7051	Intermediate Similarity	NPD2534	Approved
0.7051	Intermediate Similarity	NPD2533	Approved
0.7035	Intermediate Similarity	NPD6785	Approved
0.7035	Intermediate Similarity	NPD6784	Approved
0.7021	Intermediate Similarity	NPD17	Approved
0.7013	Intermediate Similarity	NPD7003	Approved
0.6981	Remote Similarity	NPD7458	Discontinued
0.6928	Remote Similarity	NPD1471	Phase 3
0.6923	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7819	Suspended
0.6909	Remote Similarity	NPD5494	Approved
0.6875	Remote Similarity	NPD3226	Approved
0.6875	Remote Similarity	NPD1608	Approved
0.6864	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2796	Approved
0.6839	Remote Similarity	NPD1243	Approved
0.6829	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5844	Phase 1
0.6818	Remote Similarity	NPD2346	Discontinued
0.6815	Remote Similarity	NPD7236	Approved
0.6797	Remote Similarity	NPD3748	Approved
0.6795	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3749	Approved
0.6783	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6959	Discontinued
0.6759	Remote Similarity	NPD3972	Approved
0.6755	Remote Similarity	NPD4140	Approved
0.6753	Remote Similarity	NPD6099	Approved
0.6753	Remote Similarity	NPD6100	Approved
0.6733	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2800	Approved
0.6728	Remote Similarity	NPD6599	Discontinued
0.6727	Remote Similarity	NPD7768	Phase 2
0.6726	Remote Similarity	NPD7229	Phase 3
0.6713	Remote Similarity	NPD5585	Approved
0.6712	Remote Similarity	NPD5327	Phase 3
0.6707	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD2799	Discontinued
0.6687	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD7177	Discontinued
0.6648	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD919	Approved
0.6646	Remote Similarity	NPD37	Approved
0.6645	Remote Similarity	NPD2979	Phase 3
0.6629	Remote Similarity	NPD8312	Approved
0.6629	Remote Similarity	NPD8313	Approved
0.6627	Remote Similarity	NPD4967	Phase 2
0.6627	Remote Similarity	NPD4966	Approved
0.6627	Remote Similarity	NPD4965	Approved
0.6623	Remote Similarity	NPD3764	Approved
0.6623	Remote Similarity	NPD2313	Discontinued
0.6623	Remote Similarity	NPD7097	Phase 1
0.6623	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6559	Discontinued
0.6608	Remote Similarity	NPD7473	Discontinued
0.6605	Remote Similarity	NPD7239	Suspended
0.6603	Remote Similarity	NPD6005	Phase 3
0.6603	Remote Similarity	NPD6004	Phase 3
0.6603	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD2344	Approved
0.6603	Remote Similarity	NPD6002	Phase 3
0.6603	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6355	Discontinued
0.66	Remote Similarity	NPD6832	Phase 2
0.6587	Remote Similarity	NPD7075	Discontinued
0.6582	Remote Similarity	NPD3750	Approved
0.6575	Remote Similarity	NPD1281	Approved
0.6562	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1778	Approved
0.655	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6234	Discontinued
0.6547	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5710	Approved
0.6529	Remote Similarity	NPD6232	Discontinued
0.6529	Remote Similarity	NPD5711	Approved
0.6522	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.651	Remote Similarity	NPD2797	Approved
0.651	Remote Similarity	NPD3266	Approved
0.651	Remote Similarity	NPD3267	Approved
0.6506	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD8455	Phase 2
0.6494	Remote Similarity	NPD4622	Approved
0.6494	Remote Similarity	NPD4618	Approved
0.6486	Remote Similarity	NPD4359	Approved
0.6486	Remote Similarity	NPD4107	Approved
0.6483	Remote Similarity	NPD5691	Approved
0.6478	Remote Similarity	NPD8166	Discontinued
0.6478	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD4110	Phase 3
0.6474	Remote Similarity	NPD7033	Discontinued
0.6474	Remote Similarity	NPD7228	Approved
0.6471	Remote Similarity	NPD6663	Approved
0.6471	Remote Similarity	NPD1247	Approved
0.6467	Remote Similarity	NPD3817	Phase 2
0.6464	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6799	Approved
0.6457	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7008	Discontinued
0.6446	Remote Similarity	NPD6801	Discontinued
0.6444	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD1283	Approved
0.6443	Remote Similarity	NPD1876	Approved
0.6438	Remote Similarity	NPD2309	Approved
0.6433	Remote Similarity	NPD1551	Phase 2
0.6433	Remote Similarity	NPD6808	Phase 2
0.6433	Remote Similarity	NPD2438	Suspended
0.6429	Remote Similarity	NPD4307	Phase 2
0.6424	Remote Similarity	NPD5736	Approved
0.642	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5688	Approved
0.641	Remote Similarity	NPD5689	Approved
0.641	Remote Similarity	NPD8404	Phase 2
0.6405	Remote Similarity	NPD6798	Discontinued
0.6405	Remote Similarity	NPD3268	Approved
0.6392	Remote Similarity	NPD5763	Approved
0.6392	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5762	Approved
0.6387	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5735	Approved
0.6386	Remote Similarity	NPD6385	Approved
0.6386	Remote Similarity	NPD6386	Approved
0.6386	Remote Similarity	NPD6677	Suspended
0.6383	Remote Similarity	NPD7497	Discontinued
0.6379	Remote Similarity	NPD7799	Discontinued
0.6374	Remote Similarity	NPD7199	Phase 2
0.6369	Remote Similarity	NPD5402	Approved
0.6364	Remote Similarity	NPD4870	Approved
0.6364	Remote Similarity	NPD4482	Phase 3
0.6358	Remote Similarity	NPD2798	Approved
0.6352	Remote Similarity	NPD1549	Phase 2
0.6347	Remote Similarity	NPD6280	Approved
0.6347	Remote Similarity	NPD6279	Approved
0.6347	Remote Similarity	NPD1934	Approved
0.6346	Remote Similarity	NPD6651	Approved
0.6345	Remote Similarity	NPD7644	Approved
0.634	Remote Similarity	NPD7095	Approved
0.6335	Remote Similarity	NPD3887	Approved
0.6329	Remote Similarity	NPD4477	Approved
0.6329	Remote Similarity	NPD2531	Phase 2
0.6329	Remote Similarity	NPD4476	Approved
0.6329	Remote Similarity	NPD2935	Discontinued
0.6328	Remote Similarity	NPD7240	Approved
0.6325	Remote Similarity	NPD4380	Phase 2
0.6319	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.631	Remote Similarity	NPD1465	Phase 2
0.6301	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD3926	Phase 2
0.6301	Remote Similarity	NPD9545	Approved
0.6299	Remote Similarity	NPD7985	Registered
0.6294	Remote Similarity	NPD1241	Discontinued
0.6294	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3818	Discontinued
0.6282	Remote Similarity	NPD5124	Phase 1
0.6282	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.628	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD5353	Approved
0.6266	Remote Similarity	NPD4308	Phase 3
0.6264	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6166	Phase 2
0.6259	Remote Similarity	NPD1651	Approved
0.6258	Remote Similarity	NPD6233	Phase 2
0.6257	Remote Similarity	NPD8285	Discontinued
0.6257	Remote Similarity	NPD2971	Approved
0.6257	Remote Similarity	NPD2968	Approved
0.625	Remote Similarity	NPD2897	Discontinued
0.625	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD7427	Discontinued
0.6242	Remote Similarity	NPD5403	Approved
0.6242	Remote Similarity	NPD6353	Approved
0.6236	Remote Similarity	NPD7685	Pre-registration
0.6235	Remote Similarity	NPD3882	Suspended
0.6235	Remote Similarity	NPD7057	Phase 3
0.6235	Remote Similarity	NPD7058	Phase 2

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