NPASS Compound

Structure

CID255309 OpenBabel06191716062D 32 36 0 0 1 0 0 0 0 0999 V2000 6.2304 3.8381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1722 2.9735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6311 0.5754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8778 -0.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4183 0.9607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8470 1.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3870 2.9335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5405 3.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8465 -1.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6935 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5406 0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6937 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4335 2.8824 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3261 2.4850 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2337 1.4680 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8470 0.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6935 -0.9771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8470 1.4671 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3876 1.9565 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6941 1.9562 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8470 0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8080 2.2584 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7797 2.1563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2240 1.5133 0.0000 C 0 0 0 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 2.5406 1.4675 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5595 -1.4771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4106 3.1510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9500 0.8595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2683 1.3102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 1 1 1 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 2 1 1 0 0 0 16 26 1 0 0 0 0 17 3 1 1 0 0 0 17 21 1 0 0 0 0 17 24 1 0 0 0 0 18 27 1 0 0 0 0 19 29 2 0 0 0 0 20 7 1 1 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 28 1 6 0 0 0 22 28 1 6 0 0 0 23 27 1 6 0 0 0 24 30 1 6 0 0 0 25 24 1 1 0 0 0 25 32 1 0 0 0 0 26 31 2 0 0 0 0 26 32 1 0 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.29
Volume:	474.677
LogP:	5.217
LogD:	4.601
LogS:	-4.813
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.49
Synthetic Accessibility Score:	5.129
Fsp3:	0.786
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:	-4.691
MDCK Permeability:	0.00010292684601154178
Pgp-inhibitor:	0.987
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091
Plasma Protein Binding (PPB):	89.8153305053711%
Volume Distribution (VD):	1.133
Pgp-substrate:	5.223949432373047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.352
CYP1A2-substrate:	0.255
CYP2C19-inhibitor:	0.149
CYP2C19-substrate:	0.729
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.955
CYP3A4-substrate:	0.699

ADMET: Excretion

Clearance (CL):	18.073
Half-life (T1/2):	0.084

ADMET: Toxicity

hERG Blockers:	0.366
Human Hepatotoxicity (H-HT):	0.454
Drug-inuced Liver Injury (DILI):	0.657
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.758
Skin Sensitization:	0.929
Carcinogencity:	0.67
Eye Corrosion:	0.772
Eye Irritation:	0.058
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC255309

Natural Product ID:	NPC255309
*Common Name:**	Paraminabeolide D
IUPAC Name:	(3R,4S,5R)-5-[(1S,2S)-2-[(8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxypropyl]-3,4-dimethyloxolan-2-one
Synonyms:	Paraminabeolide D
Standard InCHIKey:	UISXVQNCBCKQHL-PPGQKZPJSA-N
Standard InCHI:	InChI=1S/C28H40O4/c1-15-16(2)26(31)32-25(15)24(30)17(3)21-8-9-22-20-7-6-18-14-19(29)10-12-27(18,4)23(20)11-13-28(21,22)5/h10,12,14-17,20-25,30H,6-9,11,13H2,1-5H3/t15-,16+,17-,20-,21+,22-,23-,24-,25+,27-,28+/m0/s1
SMILES:	C[C@H]1[C@@H](C)C(=O)O[C@H]1[C@H]([C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782225
PubChem CID:	53262738
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

*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
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	Eukaryota	n.a.	the western coast of Pingtung county, Taiwan, at a depth of 10 m	2009-MAY	PMID[21425785]
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21425785]
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	43.3	%	PMID[483541]

☑ 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 NPC255309 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	200
0.1-0.2	1055
0.2-0.3	4589
0.3-0.4	9680
0.4-0.5	11499
0.5-0.6	5946
0.6-0.7	6978
0.7-0.8	2570
0.8-0.85	157
0.85-0.9	19
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC96377
0.9143	High Similarity	NPC471398
0.901	High Similarity	NPC471293
0.901	High Similarity	NPC228669
0.901	High Similarity	NPC164835
0.8942	High Similarity	NPC5284
0.8796	High Similarity	NPC284068
0.8785	High Similarity	NPC474181
0.8762	High Similarity	NPC239097
0.8725	High Similarity	NPC264048
0.8725	High Similarity	NPC140723
0.87	High Similarity	NPC114274
0.8687	High Similarity	NPC58052
0.8687	High Similarity	NPC111684
0.8667	High Similarity	NPC258543
0.8667	High Similarity	NPC241927
0.8654	High Similarity	NPC59530
0.8627	High Similarity	NPC473163
0.8614	High Similarity	NPC167974
0.86	High Similarity	NPC108078
0.8585	High Similarity	NPC37116
0.8571	High Similarity	NPC19412
0.8558	High Similarity	NPC102352
0.8532	High Similarity	NPC49492
0.8532	High Similarity	NPC266728
0.8529	High Similarity	NPC476223
0.8529	High Similarity	NPC476240
0.8529	High Similarity	NPC224720
0.8519	High Similarity	NPC250109
0.8515	High Similarity	NPC271387
0.8515	High Similarity	NPC153792
0.8505	High Similarity	NPC118860
0.8505	High Similarity	NPC231589
0.8505	High Similarity	NPC214797
0.8476	Intermediate Similarity	NPC144854
0.8476	Intermediate Similarity	NPC3316
0.8469	Intermediate Similarity	NPC218301
0.8462	Intermediate Similarity	NPC235889
0.8447	Intermediate Similarity	NPC473928
0.8438	Intermediate Similarity	NPC167877
0.8431	Intermediate Similarity	NPC218383
0.8431	Intermediate Similarity	NPC476274
0.8426	Intermediate Similarity	NPC170487
0.8426	Intermediate Similarity	NPC236217
0.8426	Intermediate Similarity	NPC152117
0.8426	Intermediate Similarity	NPC71348
0.8426	Intermediate Similarity	NPC207251
0.8426	Intermediate Similarity	NPC234042
0.8421	Intermediate Similarity	NPC8369
0.8416	Intermediate Similarity	NPC292133
0.8416	Intermediate Similarity	NPC475894
0.8411	Intermediate Similarity	NPC197428
0.8411	Intermediate Similarity	NPC473627
0.84	Intermediate Similarity	NPC469599
0.8396	Intermediate Similarity	NPC469844
0.8396	Intermediate Similarity	NPC277017
0.8396	Intermediate Similarity	NPC154608
0.8396	Intermediate Similarity	NPC192813
0.8384	Intermediate Similarity	NPC470224
0.8381	Intermediate Similarity	NPC181265
0.8381	Intermediate Similarity	NPC470309
0.8367	Intermediate Similarity	NPC289213
0.8351	Intermediate Similarity	NPC250687
0.8351	Intermediate Similarity	NPC229407
0.8351	Intermediate Similarity	NPC254572
0.8351	Intermediate Similarity	NPC48824
0.835	Intermediate Similarity	NPC472924
0.8349	Intermediate Similarity	NPC962
0.8349	Intermediate Similarity	NPC255017
0.8349	Intermediate Similarity	NPC52634
0.8318	Intermediate Similarity	NPC41405
0.8318	Intermediate Similarity	NPC153239
0.8318	Intermediate Similarity	NPC304495
0.8302	Intermediate Similarity	NPC220974
0.8302	Intermediate Similarity	NPC475294
0.8286	Intermediate Similarity	NPC100955
0.8286	Intermediate Similarity	NPC13385
0.8286	Intermediate Similarity	NPC121566
0.8283	Intermediate Similarity	NPC154101
0.8283	Intermediate Similarity	NPC19114
0.8283	Intermediate Similarity	NPC471747
0.8273	Intermediate Similarity	NPC326542
0.8269	Intermediate Similarity	NPC136289
0.8265	Intermediate Similarity	NPC269267
0.8265	Intermediate Similarity	NPC477943
0.8265	Intermediate Similarity	NPC186688
0.8257	Intermediate Similarity	NPC205534
0.8252	Intermediate Similarity	NPC287833
0.8252	Intermediate Similarity	NPC316964
0.8247	Intermediate Similarity	NPC251808
0.8247	Intermediate Similarity	NPC474174
0.8235	Intermediate Similarity	NPC27105
0.823	Intermediate Similarity	NPC474585
0.823	Intermediate Similarity	NPC109973
0.823	Intermediate Similarity	NPC476961
0.8229	Intermediate Similarity	NPC470223
0.8229	Intermediate Similarity	NPC29447
0.8224	Intermediate Similarity	NPC472825
0.8224	Intermediate Similarity	NPC258323
0.8218	Intermediate Similarity	NPC317586
0.8218	Intermediate Similarity	NPC98639
0.8218	Intermediate Similarity	NPC470016
0.8214	Intermediate Similarity	NPC475913
0.8208	Intermediate Similarity	NPC95243
0.8208	Intermediate Similarity	NPC63023
0.8208	Intermediate Similarity	NPC196528
0.8205	Intermediate Similarity	NPC473888
0.82	Intermediate Similarity	NPC474807
0.82	Intermediate Similarity	NPC206810
0.82	Intermediate Similarity	NPC474736
0.8198	Intermediate Similarity	NPC270929
0.8198	Intermediate Similarity	NPC270958
0.8198	Intermediate Similarity	NPC148458
0.8198	Intermediate Similarity	NPC190286
0.819	Intermediate Similarity	NPC474207
0.819	Intermediate Similarity	NPC282233
0.819	Intermediate Similarity	NPC471005
0.819	Intermediate Similarity	NPC95585
0.819	Intermediate Similarity	NPC277074
0.819	Intermediate Similarity	NPC474330
0.819	Intermediate Similarity	NPC209298
0.8182	Intermediate Similarity	NPC471173
0.8182	Intermediate Similarity	NPC471627
0.8174	Intermediate Similarity	NPC473979
0.8174	Intermediate Similarity	NPC469789
0.8174	Intermediate Similarity	NPC11895
0.8173	Intermediate Similarity	NPC476134
0.8173	Intermediate Similarity	NPC81530
0.8173	Intermediate Similarity	NPC474327
0.8173	Intermediate Similarity	NPC101067
0.8173	Intermediate Similarity	NPC252614
0.8163	Intermediate Similarity	NPC28227
0.8155	Intermediate Similarity	NPC197386
0.8155	Intermediate Similarity	NPC471330
0.8155	Intermediate Similarity	NPC203388
0.8155	Intermediate Similarity	NPC471331
0.8155	Intermediate Similarity	NPC472687
0.8155	Intermediate Similarity	NPC477854
0.8155	Intermediate Similarity	NPC99657
0.8148	Intermediate Similarity	NPC310546
0.8148	Intermediate Similarity	NPC470257
0.8148	Intermediate Similarity	NPC246205
0.8148	Intermediate Similarity	NPC170221
0.8148	Intermediate Similarity	NPC10064
0.8142	Intermediate Similarity	NPC475041
0.8142	Intermediate Similarity	NPC474179
0.8142	Intermediate Similarity	NPC161065
0.8142	Intermediate Similarity	NPC473203
0.8142	Intermediate Similarity	NPC475834
0.8137	Intermediate Similarity	NPC328371
0.8137	Intermediate Similarity	NPC471039
0.8137	Intermediate Similarity	NPC42042
0.8137	Intermediate Similarity	NPC29410
0.8137	Intermediate Similarity	NPC322063
0.8137	Intermediate Similarity	NPC200054
0.8131	Intermediate Similarity	NPC44063
0.8131	Intermediate Similarity	NPC230541
0.8131	Intermediate Similarity	NPC473037
0.8125	Intermediate Similarity	NPC470959
0.8125	Intermediate Similarity	NPC100391
0.8125	Intermediate Similarity	NPC476965
0.8125	Intermediate Similarity	NPC214043
0.8125	Intermediate Similarity	NPC239273
0.8125	Intermediate Similarity	NPC85774
0.8125	Intermediate Similarity	NPC471854
0.8119	Intermediate Similarity	NPC166906
0.8119	Intermediate Similarity	NPC184870
0.8119	Intermediate Similarity	NPC174051
0.8119	Intermediate Similarity	NPC473172
0.8119	Intermediate Similarity	NPC67831
0.8119	Intermediate Similarity	NPC56525
0.8113	Intermediate Similarity	NPC209502
0.8113	Intermediate Similarity	NPC96268
0.8113	Intermediate Similarity	NPC204833
0.8113	Intermediate Similarity	NPC301787
0.8113	Intermediate Similarity	NPC29705
0.8108	Intermediate Similarity	NPC473898
0.8108	Intermediate Similarity	NPC243354
0.8103	Intermediate Similarity	NPC473255
0.81	Intermediate Similarity	NPC262870
0.81	Intermediate Similarity	NPC189520
0.8095	Intermediate Similarity	NPC293753
0.8095	Intermediate Similarity	NPC22388
0.8091	Intermediate Similarity	NPC475524
0.8091	Intermediate Similarity	NPC280782
0.8091	Intermediate Similarity	NPC100267
0.8087	Intermediate Similarity	NPC170538
0.8087	Intermediate Similarity	NPC222688
0.8081	Intermediate Similarity	NPC262043
0.8081	Intermediate Similarity	NPC474570
0.8081	Intermediate Similarity	NPC476733
0.8081	Intermediate Similarity	NPC215029
0.8077	Intermediate Similarity	NPC51370
0.8077	Intermediate Similarity	NPC471041
0.8077	Intermediate Similarity	NPC474720
0.8077	Intermediate Similarity	NPC267921
0.8073	Intermediate Similarity	NPC210005
0.8073	Intermediate Similarity	NPC286880
0.8073	Intermediate Similarity	NPC76084
0.8073	Intermediate Similarity	NPC5103

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 NPC255309 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1328
0.2-0.3	3903
0.3-0.4	2526
0.4-0.5	714
0.5-0.6	175
0.6-0.7	178
0.7-0.8	143
0.8-0.85	20
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8349	Intermediate Similarity	NPD4632	Approved
0.8283	Intermediate Similarity	NPD6079	Approved
0.8257	Intermediate Similarity	NPD8297	Approved
0.8224	Intermediate Similarity	NPD6899	Approved
0.8224	Intermediate Similarity	NPD6881	Approved
0.82	Intermediate Similarity	NPD6399	Phase 3
0.8165	Intermediate Similarity	NPD6649	Approved
0.8165	Intermediate Similarity	NPD6650	Approved
0.8131	Intermediate Similarity	NPD5697	Approved
0.8103	Intermediate Similarity	NPD7492	Approved
0.8081	Intermediate Similarity	NPD5328	Approved
0.8073	Intermediate Similarity	NPD7290	Approved
0.8073	Intermediate Similarity	NPD7102	Approved
0.8073	Intermediate Similarity	NPD6883	Approved
0.807	Intermediate Similarity	NPD6319	Approved
0.807	Intermediate Similarity	NPD6054	Approved
0.8058	Intermediate Similarity	NPD6083	Phase 2
0.8058	Intermediate Similarity	NPD6084	Phase 2
0.8056	Intermediate Similarity	NPD6011	Approved
0.8056	Intermediate Similarity	NPD7320	Approved
0.8037	Intermediate Similarity	NPD7128	Approved
0.8037	Intermediate Similarity	NPD6008	Approved
0.8037	Intermediate Similarity	NPD5739	Approved
0.8037	Intermediate Similarity	NPD6675	Approved
0.8037	Intermediate Similarity	NPD6402	Approved
0.8034	Intermediate Similarity	NPD6616	Approved
0.8	Intermediate Similarity	NPD6869	Approved
0.8	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6617	Approved
0.8	Intermediate Similarity	NPD6847	Approved
0.7982	Intermediate Similarity	NPD6013	Approved
0.7982	Intermediate Similarity	NPD6372	Approved
0.7982	Intermediate Similarity	NPD6373	Approved
0.7982	Intermediate Similarity	NPD6014	Approved
0.7982	Intermediate Similarity	NPD6012	Approved
0.798	Intermediate Similarity	NPD5737	Approved
0.798	Intermediate Similarity	NPD6903	Approved
0.798	Intermediate Similarity	NPD6672	Approved
0.7966	Intermediate Similarity	NPD7078	Approved
0.7965	Intermediate Similarity	NPD6009	Approved
0.7965	Intermediate Similarity	NPD7115	Discovery
0.7963	Intermediate Similarity	NPD6412	Phase 2
0.7961	Intermediate Similarity	NPD5221	Approved
0.7961	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD5222	Approved
0.7959	Intermediate Similarity	NPD6409	Approved
0.7959	Intermediate Similarity	NPD6684	Approved
0.7959	Intermediate Similarity	NPD5330	Approved
0.7959	Intermediate Similarity	NPD7146	Approved
0.7959	Intermediate Similarity	NPD7521	Approved
0.7959	Intermediate Similarity	NPD7334	Approved
0.7931	Intermediate Similarity	NPD6370	Approved
0.7928	Intermediate Similarity	NPD6882	Approved
0.7899	Intermediate Similarity	NPD7736	Approved
0.7885	Intermediate Similarity	NPD5173	Approved
0.7864	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD7604	Phase 2
0.7845	Intermediate Similarity	NPD6015	Approved
0.7845	Intermediate Similarity	NPD5983	Phase 2
0.7845	Intermediate Similarity	NPD6016	Approved
0.781	Intermediate Similarity	NPD5696	Approved
0.78	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD5701	Approved
0.7788	Intermediate Similarity	NPD4697	Phase 3
0.7778	Intermediate Similarity	NPD3618	Phase 1
0.7778	Intermediate Similarity	NPD5988	Approved
0.7759	Intermediate Similarity	NPD6059	Approved
0.7755	Intermediate Similarity	NPD4786	Approved
0.7755	Intermediate Similarity	NPD3666	Approved
0.7755	Intermediate Similarity	NPD3133	Approved
0.7755	Intermediate Similarity	NPD3665	Phase 1
0.7748	Intermediate Similarity	NPD4634	Approved
0.7736	Intermediate Similarity	NPD4696	Approved
0.7736	Intermediate Similarity	NPD5285	Approved
0.7736	Intermediate Similarity	NPD5286	Approved
0.7731	Intermediate Similarity	NPD6336	Discontinued
0.7719	Intermediate Similarity	NPD6868	Approved
0.7692	Intermediate Similarity	NPD4629	Approved
0.7692	Intermediate Similarity	NPD5210	Approved
0.7692	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5695	Phase 3
0.7679	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8293	Discontinued
0.7664	Intermediate Similarity	NPD5223	Approved
0.7647	Intermediate Similarity	NPD5207	Approved
0.7642	Intermediate Similarity	NPD7638	Approved
0.7596	Intermediate Similarity	NPD7748	Approved
0.7593	Intermediate Similarity	NPD5224	Approved
0.7593	Intermediate Similarity	NPD5225	Approved
0.7593	Intermediate Similarity	NPD4633	Approved
0.7593	Intermediate Similarity	NPD5226	Approved
0.7593	Intermediate Similarity	NPD5211	Phase 2
0.7586	Intermediate Similarity	NPD6335	Approved
0.7573	Intermediate Similarity	NPD5281	Approved
0.7573	Intermediate Similarity	NPD7515	Phase 2
0.7573	Intermediate Similarity	NPD5284	Approved
0.757	Intermediate Similarity	NPD7639	Approved
0.757	Intermediate Similarity	NPD7640	Approved
0.7568	Intermediate Similarity	NPD6686	Approved
0.7551	Intermediate Similarity	NPD3667	Approved
0.7549	Intermediate Similarity	NPD6904	Approved
0.7549	Intermediate Similarity	NPD6080	Approved
0.7549	Intermediate Similarity	NPD4753	Phase 2
0.7549	Intermediate Similarity	NPD6673	Approved
0.7547	Intermediate Similarity	NPD7902	Approved
0.7547	Intermediate Similarity	NPD4755	Approved
0.7523	Intermediate Similarity	NPD5175	Approved
0.7523	Intermediate Similarity	NPD5174	Approved
0.7521	Intermediate Similarity	NPD7101	Approved
0.7521	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD6317	Approved
0.7455	Intermediate Similarity	NPD5141	Approved
0.7438	Intermediate Similarity	NPD7507	Approved
0.7436	Intermediate Similarity	NPD6314	Approved
0.7436	Intermediate Similarity	NPD6313	Approved
0.7429	Intermediate Similarity	NPD6001	Approved
0.7426	Intermediate Similarity	NPD5279	Phase 3
0.7414	Intermediate Similarity	NPD6274	Approved
0.7407	Intermediate Similarity	NPD4700	Approved
0.7374	Intermediate Similarity	NPD4221	Approved
0.7374	Intermediate Similarity	NPD4223	Phase 3
0.7353	Intermediate Similarity	NPD3573	Approved
0.7333	Intermediate Similarity	NPD4202	Approved
0.7327	Intermediate Similarity	NPD5329	Approved
0.7317	Intermediate Similarity	NPD6033	Approved
0.7315	Intermediate Similarity	NPD4225	Approved
0.7304	Intermediate Similarity	NPD6053	Discontinued
0.7282	Intermediate Similarity	NPD5208	Approved
0.7273	Intermediate Similarity	NPD8328	Phase 3
0.7264	Intermediate Similarity	NPD7900	Approved
0.7264	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7319	Approved
0.7257	Intermediate Similarity	NPD4730	Approved
0.7257	Intermediate Similarity	NPD5168	Approved
0.7257	Intermediate Similarity	NPD4729	Approved
0.7255	Intermediate Similarity	NPD5690	Phase 2
0.7255	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6098	Approved
0.7238	Intermediate Similarity	NPD5693	Phase 1
0.7238	Intermediate Similarity	NPD8035	Phase 2
0.7238	Intermediate Similarity	NPD6050	Approved
0.7238	Intermediate Similarity	NPD6411	Approved
0.7238	Intermediate Similarity	NPD5694	Approved
0.7238	Intermediate Similarity	NPD8034	Phase 2
0.7228	Intermediate Similarity	NPD4197	Approved
0.7207	Intermediate Similarity	NPD6052	Approved
0.7207	Intermediate Similarity	NPD4754	Approved
0.7196	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD1694	Approved
0.7157	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7131	Intermediate Similarity	NPD6067	Discontinued
0.713	Intermediate Similarity	NPD5251	Approved
0.713	Intermediate Similarity	NPD5169	Approved
0.713	Intermediate Similarity	NPD5250	Approved
0.713	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD5249	Phase 3
0.713	Intermediate Similarity	NPD5248	Approved
0.713	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5135	Approved
0.7129	Intermediate Similarity	NPD4788	Approved
0.7107	Intermediate Similarity	NPD6909	Approved
0.7107	Intermediate Similarity	NPD6908	Approved
0.7105	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5128	Approved
0.7087	Intermediate Similarity	NPD4693	Phase 3
0.7087	Intermediate Similarity	NPD4689	Approved
0.7087	Intermediate Similarity	NPD5205	Approved
0.7087	Intermediate Similarity	NPD4688	Approved
0.7087	Intermediate Similarity	NPD4138	Approved
0.7087	Intermediate Similarity	NPD4690	Approved
0.708	Intermediate Similarity	NPD4767	Approved
0.708	Intermediate Similarity	NPD4768	Approved
0.7075	Intermediate Similarity	NPD7637	Suspended
0.7071	Intermediate Similarity	NPD4195	Approved
0.7069	Intermediate Similarity	NPD5216	Approved
0.7069	Intermediate Similarity	NPD5215	Approved
0.7069	Intermediate Similarity	NPD5127	Approved
0.7069	Intermediate Similarity	NPD5217	Approved
0.7063	Intermediate Similarity	NPD5956	Approved
0.7059	Intermediate Similarity	NPD3668	Phase 3
0.7048	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6101	Approved
0.7043	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6435	Approved
0.703	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6614	Approved
0.7009	Intermediate Similarity	NPD5778	Approved
0.7009	Intermediate Similarity	NPD5779	Approved
0.7008	Intermediate Similarity	NPD7260	Phase 2
0.7	Intermediate Similarity	NPD4695	Discontinued
0.6981	Remote Similarity	NPD5785	Approved
0.697	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3617	Approved
0.6967	Remote Similarity	NPD7503	Approved
0.6964	Remote Similarity	NPD7632	Discontinued
0.6942	Remote Similarity	NPD4522	Approved
0.6923	Remote Similarity	NPD4694	Approved
0.6923	Remote Similarity	NPD5280	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