NPASS Compound

Structure

NPC293223 OpenBabel07101718292D 24 26 0 0 1 0 0 0 0 0999 V2000 1.5388 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6923 1.8035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 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 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 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 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9021 0.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5013 1.2158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 13 11 1 6 0 0 0 13 17 1 0 0 0 0 14 10 1 6 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 20 1 6 0 0 0 15 21 1 0 0 0 0 16 12 1 1 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.25
Volume:	361.331
LogP:	3.134
LogD:	3.201
LogS:	-3.252
# Rotatable Bonds:	1
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	5.951
Fsp3:	0.9
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:	-4.657
MDCK Permeability:	1.587302722327877e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.093
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107
Plasma Protein Binding (PPB):	81.42852020263672%
Volume Distribution (VD):	1.458
Pgp-substrate:	10.495701789855957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.153
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.783
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.138
CYP3A4-substrate:	0.476

ADMET: Excretion

Clearance (CL):	7.507
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.329
Drug-inuced Liver Injury (DILI):	0.165
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.037
Carcinogencity:	0.043
Eye Corrosion:	0.023
Eye Irritation:	0.098
Respiratory Toxicity:	0.338

Download Data

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

Natural Product: NPC293223

Natural Product ID:	NPC293223
*Common Name:**	Sclerophytin A
IUPAC Name:	n.a.
Synonyms:	Sclerophytin A
Standard InCHIKey:	BEAXQAULPSVWQY-QXXRKKQISA-N
Standard InCHI:	InChI=1S/C20H34O4/c1-11(2)13-7-6-12(3)16-14-10-20(5,23)15(21)8-9-19(4,22)18(24-14)17(13)16/h11,13-18,21-23H,3,6-10H2,1-2,4-5H3/t13-,14-,15+,16-,17-,18-,19-,20+/m1/s1
SMILES:	CC(C)[C@H]1CCC(=C)[C@@H]2[C@H]3C[C@@](C)([C@H](CC[C@](C)([C@@H]([C@H]12)O3)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096773
PubChem CID:	11325231
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002916] Eunicellane and asbestinane 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
NPO3452	Virgularia juncea	Species	Virgulariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575967]
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	Eukaryota	n.a.	red sea soft coral	n.a.	PMID[20420415]
NPO32470	octocorallia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[21970540]
NPO3452	Virgularia juncea	Species	Virgulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22114	Cladiella pachyclados	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
ED50	1
IC50	4

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.3	ug ml-1	PMID[514040]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	84000.0	nM	PMID[514042]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	11904769.75	nM	PMID[514042]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	3.0	nM	PMID[514043]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	57000.0	nM	PMID[514043]

☑ 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 NPC293223 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	162
0.1-0.2	1883
0.2-0.3	7269
0.3-0.4	15798
0.4-0.5	7346
0.5-0.6	8173
0.6-0.7	1951
0.7-0.8	87
0.8-0.85	16
0.85-0.9	6
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC36479
0.9444	High Similarity	NPC329626
0.9333	High Similarity	NPC118116
0.9091	High Similarity	NPC239308
0.8861	High Similarity	NPC196911
0.8861	High Similarity	NPC471379
0.8831	High Similarity	NPC77003
0.8718	High Similarity	NPC103171
0.8608	High Similarity	NPC5958
0.8533	High Similarity	NPC12696
0.8519	High Similarity	NPC475684
0.8415	Intermediate Similarity	NPC44538
0.8333	Intermediate Similarity	NPC312471
0.8333	Intermediate Similarity	NPC471378
0.8313	Intermediate Similarity	NPC75443
0.8313	Intermediate Similarity	NPC92370
0.8313	Intermediate Similarity	NPC476723
0.8313	Intermediate Similarity	NPC309656
0.8313	Intermediate Similarity	NPC476724
0.8313	Intermediate Similarity	NPC470260
0.8293	Intermediate Similarity	NPC322922
0.8293	Intermediate Similarity	NPC321812
0.8235	Intermediate Similarity	NPC122057
0.8214	Intermediate Similarity	NPC291875
0.8214	Intermediate Similarity	NPC161560
0.8205	Intermediate Similarity	NPC264610
0.8026	Intermediate Similarity	NPC476709
0.8023	Intermediate Similarity	NPC91251
0.8023	Intermediate Similarity	NPC312805
0.7952	Intermediate Similarity	NPC476725
0.7927	Intermediate Similarity	NPC127917
0.7875	Intermediate Similarity	NPC476701
0.7848	Intermediate Similarity	NPC476703
0.7816	Intermediate Similarity	NPC208839
0.7792	Intermediate Similarity	NPC143576
0.7778	Intermediate Similarity	NPC76054
0.775	Intermediate Similarity	NPC52755
0.7738	Intermediate Similarity	NPC290731
0.7722	Intermediate Similarity	NPC136424
0.7674	Intermediate Similarity	NPC473436
0.7674	Intermediate Similarity	NPC22376
0.7647	Intermediate Similarity	NPC476217
0.7632	Intermediate Similarity	NPC16964
0.7582	Intermediate Similarity	NPC111348
0.7568	Intermediate Similarity	NPC250836
0.7531	Intermediate Similarity	NPC43463
0.7531	Intermediate Similarity	NPC191345
0.7531	Intermediate Similarity	NPC477089
0.7531	Intermediate Similarity	NPC252483
0.75	Intermediate Similarity	NPC159876
0.7473	Intermediate Similarity	NPC8803
0.7442	Intermediate Similarity	NPC214315
0.7439	Intermediate Similarity	NPC476367
0.7439	Intermediate Similarity	NPC72755
0.7436	Intermediate Similarity	NPC306085
0.7432	Intermediate Similarity	NPC476702
0.7416	Intermediate Similarity	NPC210268
0.7416	Intermediate Similarity	NPC8729
0.7412	Intermediate Similarity	NPC83702
0.7412	Intermediate Similarity	NPC242016
0.7407	Intermediate Similarity	NPC476719
0.7386	Intermediate Similarity	NPC473058
0.7386	Intermediate Similarity	NPC97103
0.7386	Intermediate Similarity	NPC115607
0.7375	Intermediate Similarity	NPC472950
0.7375	Intermediate Similarity	NPC472952
0.7363	Intermediate Similarity	NPC476720
0.7356	Intermediate Similarity	NPC251808
0.7356	Intermediate Similarity	NPC189777
0.7356	Intermediate Similarity	NPC474174
0.7342	Intermediate Similarity	NPC95165
0.7333	Intermediate Similarity	NPC119379
0.7333	Intermediate Similarity	NPC98193
0.7326	Intermediate Similarity	NPC298595
0.7317	Intermediate Similarity	NPC3852
0.7303	Intermediate Similarity	NPC191323
0.7303	Intermediate Similarity	NPC470832
0.7294	Intermediate Similarity	NPC216420
0.7294	Intermediate Similarity	NPC85095
0.7294	Intermediate Similarity	NPC211135
0.7284	Intermediate Similarity	NPC170148
0.7273	Intermediate Similarity	NPC319030
0.7262	Intermediate Similarity	NPC5361
0.7262	Intermediate Similarity	NPC211049
0.7253	Intermediate Similarity	NPC39453
0.7241	Intermediate Similarity	NPC121981
0.7241	Intermediate Similarity	NPC247826
0.7234	Intermediate Similarity	NPC272223
0.7222	Intermediate Similarity	NPC219516
0.7222	Intermediate Similarity	NPC302584
0.7222	Intermediate Similarity	NPC165180
0.7216	Intermediate Similarity	NPC470263
0.7209	Intermediate Similarity	NPC86238
0.7209	Intermediate Similarity	NPC255882
0.7209	Intermediate Similarity	NPC319238
0.7209	Intermediate Similarity	NPC166279
0.7204	Intermediate Similarity	NPC26307
0.7179	Intermediate Similarity	NPC234511
0.7174	Intermediate Similarity	NPC286612
0.7174	Intermediate Similarity	NPC275310
0.7174	Intermediate Similarity	NPC230347
0.7159	Intermediate Similarity	NPC476948
0.7143	Intermediate Similarity	NPC474792
0.7143	Intermediate Similarity	NPC91654
0.7143	Intermediate Similarity	NPC186594
0.7143	Intermediate Similarity	NPC161612
0.7143	Intermediate Similarity	NPC474592
0.7143	Intermediate Similarity	NPC67398
0.7143	Intermediate Similarity	NPC100697
0.7143	Intermediate Similarity	NPC474835
0.7143	Intermediate Similarity	NPC33583
0.7128	Intermediate Similarity	NPC309493
0.7128	Intermediate Similarity	NPC216260
0.7128	Intermediate Similarity	NPC5358
0.7111	Intermediate Similarity	NPC206614
0.7111	Intermediate Similarity	NPC474323
0.7105	Intermediate Similarity	NPC471200
0.7097	Intermediate Similarity	NPC472989
0.7097	Intermediate Similarity	NPC210717
0.7097	Intermediate Similarity	NPC103165
0.7093	Intermediate Similarity	NPC477978
0.7093	Intermediate Similarity	NPC232023
0.7093	Intermediate Similarity	NPC320548
0.7089	Intermediate Similarity	NPC470041
0.7079	Intermediate Similarity	NPC48824
0.7079	Intermediate Similarity	NPC229407
0.7079	Intermediate Similarity	NPC250687
0.7079	Intermediate Similarity	NPC254572
0.7073	Intermediate Similarity	NPC236228
0.7073	Intermediate Similarity	NPC274079
0.7073	Intermediate Similarity	NPC477925
0.7073	Intermediate Similarity	NPC470766
0.7073	Intermediate Similarity	NPC63958
0.7073	Intermediate Similarity	NPC256720
0.7067	Intermediate Similarity	NPC50435
0.7065	Intermediate Similarity	NPC72817
0.7065	Intermediate Similarity	NPC96736
0.7065	Intermediate Similarity	NPC178949
0.7065	Intermediate Similarity	NPC473258
0.7065	Intermediate Similarity	NPC477927
0.7065	Intermediate Similarity	NPC476722
0.7059	Intermediate Similarity	NPC116320
0.7059	Intermediate Similarity	NPC119922
0.7053	Intermediate Similarity	NPC473790
0.7051	Intermediate Similarity	NPC266578
0.7045	Intermediate Similarity	NPC145245
0.7045	Intermediate Similarity	NPC470836
0.7037	Intermediate Similarity	NPC470151
0.7037	Intermediate Similarity	NPC190859
0.7033	Intermediate Similarity	NPC471747
0.7033	Intermediate Similarity	NPC114389
0.7024	Intermediate Similarity	NPC233295
0.7021	Intermediate Similarity	NPC261807
0.7021	Intermediate Similarity	NPC76486
0.7021	Intermediate Similarity	NPC473890
0.7021	Intermediate Similarity	NPC243728
0.7021	Intermediate Similarity	NPC473244
0.7011	Intermediate Similarity	NPC151176
0.7011	Intermediate Similarity	NPC299963
0.7011	Intermediate Similarity	NPC3464
0.7011	Intermediate Similarity	NPC475963
0.701	Intermediate Similarity	NPC475701
0.7	Intermediate Similarity	NPC133450
0.7	Intermediate Similarity	NPC128066
0.7	Intermediate Similarity	NPC77001
0.7	Intermediate Similarity	NPC253618
0.7	Intermediate Similarity	NPC269267
0.7	Intermediate Similarity	NPC477917
0.6989	Remote Similarity	NPC473348
0.6989	Remote Similarity	NPC292178
0.6989	Remote Similarity	NPC86893
0.6989	Remote Similarity	NPC30477
0.6989	Remote Similarity	NPC8774
0.6988	Remote Similarity	NPC477924
0.6988	Remote Similarity	NPC130136
0.6979	Remote Similarity	NPC98225
0.6977	Remote Similarity	NPC477390
0.6977	Remote Similarity	NPC477385
0.6977	Remote Similarity	NPC216800
0.6966	Remote Similarity	NPC233744
0.6962	Remote Similarity	NPC472947
0.6957	Remote Similarity	NPC296620
0.6957	Remote Similarity	NPC137461
0.6947	Remote Similarity	NPC476895
0.6947	Remote Similarity	NPC470066
0.6947	Remote Similarity	NPC470067
0.6947	Remote Similarity	NPC275865
0.6947	Remote Similarity	NPC158088
0.6947	Remote Similarity	NPC470068
0.6941	Remote Similarity	NPC71535
0.6941	Remote Similarity	NPC472951
0.6941	Remote Similarity	NPC287749
0.6941	Remote Similarity	NPC78545
0.6941	Remote Similarity	NPC472943
0.6939	Remote Similarity	NPC474464
0.6932	Remote Similarity	NPC476715
0.6923	Remote Similarity	NPC261990
0.6923	Remote Similarity	NPC269077
0.6923	Remote Similarity	NPC474249
0.6923	Remote Similarity	NPC253303

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 NPC293223 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	2602
0.2-0.3	4026
0.3-0.4	1634
0.4-0.5	430
0.5-0.6	271
0.6-0.7	33
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7356	Intermediate Similarity	NPD7524	Approved
0.7209	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6695	Phase 3
0.6867	Remote Similarity	NPD6933	Approved
0.6778	Remote Similarity	NPD7750	Discontinued
0.6744	Remote Similarity	NPD6930	Phase 2
0.6744	Remote Similarity	NPD6931	Approved
0.6633	Remote Similarity	NPD5344	Discontinued
0.6628	Remote Similarity	NPD6929	Approved
0.6627	Remote Similarity	NPD6924	Approved
0.6627	Remote Similarity	NPD6926	Approved
0.6588	Remote Similarity	NPD6932	Approved
0.6579	Remote Similarity	NPD1145	Discontinued
0.6559	Remote Similarity	NPD3168	Discontinued
0.6552	Remote Similarity	NPD7525	Registered
0.6538	Remote Similarity	NPD371	Approved
0.6489	Remote Similarity	NPD7087	Discontinued
0.6437	Remote Similarity	NPD6683	Phase 2
0.6395	Remote Similarity	NPD5776	Phase 2
0.6395	Remote Similarity	NPD6925	Approved
0.6383	Remote Similarity	NPD6698	Approved
0.6383	Remote Similarity	NPD46	Approved
0.6383	Remote Similarity	NPD7838	Discovery
0.6374	Remote Similarity	NPD6893	Approved
0.6364	Remote Similarity	NPD7514	Phase 3
0.6364	Remote Similarity	NPD7509	Discontinued
0.6364	Remote Similarity	NPD7332	Phase 2
0.6353	Remote Similarity	NPD6942	Approved
0.6353	Remote Similarity	NPD7339	Approved
0.6322	Remote Similarity	NPD7145	Approved
0.6311	Remote Similarity	NPD6412	Phase 2
0.6292	Remote Similarity	NPD6898	Phase 1
0.6279	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD7645	Phase 2
0.62	Remote Similarity	NPD6648	Approved
0.6186	Remote Similarity	NPD5282	Discontinued
0.6146	Remote Similarity	NPD7983	Approved
0.6145	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD6923	Approved
0.6145	Remote Similarity	NPD6922	Approved
0.6111	Remote Similarity	NPD6902	Approved
0.6111	Remote Similarity	NPD8133	Approved
0.6071	Remote Similarity	NPD7144	Approved
0.6071	Remote Similarity	NPD7143	Approved
0.6064	Remote Similarity	NPD4251	Approved
0.6064	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4250	Approved
0.6058	Remote Similarity	NPD5357	Phase 1
0.6047	Remote Similarity	NPD1810	Approved
0.6047	Remote Similarity	NPD1811	Approved
0.6	Remote Similarity	NPD7150	Approved
0.6	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7151	Approved
0.6	Remote Similarity	NPD7152	Approved
0.5979	Remote Similarity	NPD7637	Suspended
0.5957	Remote Similarity	NPD4249	Approved
0.5955	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7638	Approved
0.5926	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5778	Approved
0.5918	Remote Similarity	NPD8171	Discontinued
0.5918	Remote Similarity	NPD6399	Phase 3
0.5918	Remote Similarity	NPD5779	Approved
0.5914	Remote Similarity	NPD4786	Approved
0.5905	Remote Similarity	NPD6640	Phase 3
0.5893	Remote Similarity	NPD7327	Approved
0.5893	Remote Similarity	NPD7328	Approved
0.5888	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7640	Approved
0.5882	Remote Similarity	NPD7639	Approved
0.5877	Remote Similarity	NPD8033	Approved
0.5875	Remote Similarity	NPD368	Approved
0.587	Remote Similarity	NPD3667	Approved
0.5862	Remote Similarity	NPD4785	Approved
0.5862	Remote Similarity	NPD4784	Approved
0.5841	Remote Similarity	NPD7516	Approved
0.5833	Remote Similarity	NPD6371	Approved
0.5824	Remote Similarity	NPD4821	Approved
0.5824	Remote Similarity	NPD4819	Approved
0.5824	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD6928	Phase 2
0.5824	Remote Similarity	NPD4820	Approved
0.5824	Remote Similarity	NPD4748	Discontinued
0.5824	Remote Similarity	NPD4822	Approved
0.5816	Remote Similarity	NPD8034	Phase 2
0.5816	Remote Similarity	NPD8035	Phase 2
0.5814	Remote Similarity	NPD4243	Approved
0.5806	Remote Similarity	NPD4788	Approved
0.5795	Remote Similarity	NPD8264	Approved
0.5789	Remote Similarity	NPD6059	Approved
0.5789	Remote Similarity	NPD8377	Approved
0.5789	Remote Similarity	NPD8294	Approved
0.5789	Remote Similarity	NPD6054	Approved
0.5784	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD6101	Approved
0.5741	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD8380	Approved
0.5739	Remote Similarity	NPD7503	Approved
0.5739	Remote Similarity	NPD8296	Approved
0.5739	Remote Similarity	NPD8379	Approved
0.5739	Remote Similarity	NPD8335	Approved
0.5739	Remote Similarity	NPD8378	Approved
0.5727	Remote Similarity	NPD6053	Discontinued
0.5714	Remote Similarity	NPD7136	Phase 2
0.5699	Remote Similarity	NPD6435	Approved
0.5698	Remote Similarity	NPD2687	Approved
0.5698	Remote Similarity	NPD2254	Approved
0.5698	Remote Similarity	NPD2686	Approved
0.569	Remote Similarity	NPD6370	Approved
0.5686	Remote Similarity	NPD6084	Phase 2
0.5686	Remote Similarity	NPD6083	Phase 2
0.5684	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD4632	Approved
0.5673	Remote Similarity	NPD4159	Approved
0.5657	Remote Similarity	NPD6411	Approved
0.5652	Remote Similarity	NPD6319	Approved
0.5641	Remote Similarity	NPD2267	Suspended
0.5638	Remote Similarity	NPD7154	Phase 3
0.5638	Remote Similarity	NPD6110	Phase 1
0.5612	Remote Similarity	NPD4753	Phase 2
0.5607	Remote Similarity	NPD5739	Approved
0.5607	Remote Similarity	NPD6402	Approved
0.5607	Remote Similarity	NPD7128	Approved
0.5607	Remote Similarity	NPD6675	Approved
0.5604	Remote Similarity	NPD4268	Approved
0.5604	Remote Similarity	NPD4271	Approved
0.5603	Remote Similarity	NPD6015	Approved
0.5603	Remote Similarity	NPD6016	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