NPASS Compound

Structure

NPC470253 OpenBabel07101719242D 23 26 0 0 1 0 0 0 0 0999 V2000 0.2588 0.9659 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 -1.0000 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 0.7934 -0.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 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 -4.3301 1.5000 0.0000 C 0 0 0 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 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 1.7172 -0.2261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 1 0 0 0 0 2 8 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 17 1 0 0 0 0 6 7 2 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 13 3 1 6 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 15 16 2 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 1 0 0 0 18 22 2 0 0 0 0 19 23 2 0 0 0 0 20 1 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.14
Volume:	328.166
LogP:	4.063
LogD:	3.21
LogS:	-4.566
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.47
Synthetic Accessibility Score:	3.278
Fsp3:	0.3
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:	-4.817
MDCK Permeability:	1.699588574410882e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.694
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	96.81928253173828%
Volume Distribution (VD):	0.707
Pgp-substrate:	2.6787519454956055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.57
CYP2C19-inhibitor:	0.245
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.368
CYP2C9-substrate:	0.745
CYP2D6-inhibitor:	0.661
CYP2D6-substrate:	0.851
CYP3A4-inhibitor:	0.543
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	15.043
Half-life (T1/2):	0.367

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.658
AMES Toxicity:	0.849
Rat Oral Acute Toxicity:	0.382
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.956
Carcinogencity:	0.808
Eye Corrosion:	0.004
Eye Irritation:	0.903
Respiratory Toxicity:	0.427

Download Data

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

Natural Product: NPC470253

Natural Product ID:	NPC470253
*Common Name:**	Neopetrosiquinone B
IUPAC Name:	(4S,4aR,12bS)-4-(hydroxymethyl)-4-methyl-2,3,4a,12b-tetrahydro-1H-benzo[a]anthracene-8,11-dione
Synonyms:	Neopetrosiquinone B
Standard InCHIKey:	YSDRXIHONJGJIN-YXKFXFPPSA-N
Standard InCHI:	InChI=1S/C20H20O3/c1-20(11-21)8-2-3-13-14-10-16-15(18(22)6-7-19(16)23)9-12(14)4-5-17(13)20/h4-7,9-10,13,17,21H,2-3,8,11H2,1H3/t13-,17-,20-/m1/s1
SMILES:	C[C@]1(CO)CCC[C@H]2[C@H]1C=Cc1c2cc2c(c1)C(=O)C=CC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1917936
PubChem CID:	57400936
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO33049	Neopetrosia cf. proxima	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014756]
NPO33049	Neopetrosia cf. proxima	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25906329]

☑ 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	8
Others	24

Activity Type	# Activity
Cell Line	31
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	15500.0	nM	PMID[568105]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	13800.0	nM	PMID[568105]
NPT2297	Cell Line	ASPC1	Homo sapiens	IC50	>	15500.0	nM	PMID[568105]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	9800.0	nM	PMID[568105]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	17.0	%	PMID[568106]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	12.0	%	PMID[568106]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	16.0	%	PMID[568106]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	67.0	%	PMID[568106]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	62.0	%	PMID[568106]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	6.1	%	PMID[568106]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	4.0	%	PMID[568106]
NPT2424	Cell Line	T84	Homo sapiens	IC50	=	11500.0	nM	PMID[568106]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7700.0	nM	PMID[568106]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8300.0	nM	PMID[568106]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	15.0	%	PMID[568106]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	32.0	%	PMID[568106]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	93.0	%	PMID[568106]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	39.0	%	PMID[568106]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	5.0	%	PMID[568106]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	12.0	%	PMID[568106]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.7	%	PMID[568106]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	17.0	%	PMID[568106]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	1.7	%	PMID[568106]
NPT2424	Cell Line	T84	Homo sapiens	Activity	=	6.2	%	PMID[568106]
NPT2424	Cell Line	T84	Homo sapiens	Activity	=	14.0	%	PMID[568106]
NPT2424	Cell Line	T84	Homo sapiens	Activity	=	59.0	%	PMID[568106]
NPT2424	Cell Line	T84	Homo sapiens	Activity	=	71.0	%	PMID[568106]
NPT2424	Cell Line	T84	Homo sapiens	Activity	=	17.0	%	PMID[568106]
NPT2424	Cell Line	T84	Homo sapiens	Activity	=	9.0	%	PMID[568106]
NPT2424	Cell Line	T84	Homo sapiens	Activity	=	18.0	%	PMID[568106]
NPT2424	Cell Line	T84	Homo sapiens	Activity	=	7.1	%	PMID[568106]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	15500.0	nM	PMID[568105]

☑ 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 NPC470253 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	1057
0.2-0.3	2067
0.3-0.4	7307
0.4-0.5	14622
0.5-0.6	14093
0.6-0.7	2841
0.7-0.8	425
0.8-0.85	50
0.85-0.9	27
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9434	High Similarity	NPC265513
0.9091	High Similarity	NPC215419
0.9018	High Similarity	NPC80605
0.9018	High Similarity	NPC222968
0.9018	High Similarity	NPC323440
0.8952	High Similarity	NPC247976
0.8909	High Similarity	NPC143768
0.8785	High Similarity	NPC471186
0.8772	High Similarity	NPC318173
0.8762	High Similarity	NPC476993
0.8761	High Similarity	NPC469843
0.875	High Similarity	NPC75724
0.875	High Similarity	NPC134882
0.8739	High Similarity	NPC93287
0.8704	High Similarity	NPC100767
0.8696	High Similarity	NPC202015
0.8654	High Similarity	NPC265220
0.8654	High Similarity	NPC239185
0.8585	High Similarity	NPC109514
0.8547	High Similarity	NPC472981
0.8545	High Similarity	NPC470252
0.8534	High Similarity	NPC476645
0.8519	High Similarity	NPC329282
0.8496	Intermediate Similarity	NPC326664
0.8496	Intermediate Similarity	NPC471721
0.8487	Intermediate Similarity	NPC328107
0.8482	Intermediate Similarity	NPC292834
0.8482	Intermediate Similarity	NPC218855
0.8482	Intermediate Similarity	NPC280789
0.8462	Intermediate Similarity	NPC260233
0.8455	Intermediate Similarity	NPC112903
0.8396	Intermediate Similarity	NPC49994
0.8381	Intermediate Similarity	NPC219573
0.8381	Intermediate Similarity	NPC185208
0.8365	Intermediate Similarity	NPC238219
0.8364	Intermediate Similarity	NPC185763
0.8364	Intermediate Similarity	NPC94751
0.8364	Intermediate Similarity	NPC83409
0.8364	Intermediate Similarity	NPC142326
0.8361	Intermediate Similarity	NPC478162
0.8361	Intermediate Similarity	NPC478165
0.8333	Intermediate Similarity	NPC196673
0.8333	Intermediate Similarity	NPC234637
0.8333	Intermediate Similarity	NPC130591
0.8319	Intermediate Similarity	NPC471188
0.8319	Intermediate Similarity	NPC471189
0.8319	Intermediate Similarity	NPC186128
0.8305	Intermediate Similarity	NPC472679
0.8305	Intermediate Similarity	NPC472680
0.8273	Intermediate Similarity	NPC172483
0.8269	Intermediate Similarity	NPC59677
0.8269	Intermediate Similarity	NPC153885
0.8269	Intermediate Similarity	NPC323420
0.8269	Intermediate Similarity	NPC155232
0.8246	Intermediate Similarity	NPC471481
0.8241	Intermediate Similarity	NPC128248
0.8241	Intermediate Similarity	NPC225079
0.8241	Intermediate Similarity	NPC133809
0.8241	Intermediate Similarity	NPC136810
0.823	Intermediate Similarity	NPC474057
0.8182	Intermediate Similarity	NPC318067
0.8173	Intermediate Similarity	NPC133461
0.8108	Intermediate Similarity	NPC134120
0.8103	Intermediate Similarity	NPC217111
0.8095	Intermediate Similarity	NPC188844
0.8095	Intermediate Similarity	NPC1682
0.8091	Intermediate Similarity	NPC274443
0.8091	Intermediate Similarity	NPC329556
0.8083	Intermediate Similarity	NPC476234
0.8077	Intermediate Similarity	NPC173413
0.8065	Intermediate Similarity	NPC51448
0.8065	Intermediate Similarity	NPC115797
0.8033	Intermediate Similarity	NPC85511
0.8033	Intermediate Similarity	NPC472681
0.8019	Intermediate Similarity	NPC289883
0.8017	Intermediate Similarity	NPC269923
0.8017	Intermediate Similarity	NPC167323
0.8017	Intermediate Similarity	NPC67377
0.8	Intermediate Similarity	NPC222390
0.8	Intermediate Similarity	NPC244427
0.8	Intermediate Similarity	NPC284475
0.8	Intermediate Similarity	NPC220596
0.7984	Intermediate Similarity	NPC474106
0.7982	Intermediate Similarity	NPC221825
0.7963	Intermediate Similarity	NPC226041
0.7949	Intermediate Similarity	NPC93181
0.7949	Intermediate Similarity	NPC474095
0.7917	Intermediate Similarity	NPC204784
0.7913	Intermediate Similarity	NPC137315
0.7899	Intermediate Similarity	NPC61651
0.789	Intermediate Similarity	NPC329387
0.789	Intermediate Similarity	NPC317280
0.7885	Intermediate Similarity	NPC157778
0.7881	Intermediate Similarity	NPC9274
0.7881	Intermediate Similarity	NPC260886
0.7876	Intermediate Similarity	NPC37914
0.7851	Intermediate Similarity	NPC238861
0.7851	Intermediate Similarity	NPC77000
0.7845	Intermediate Similarity	NPC66208
0.7833	Intermediate Similarity	NPC472697
0.7833	Intermediate Similarity	NPC472698
0.7823	Intermediate Similarity	NPC295664
0.7815	Intermediate Similarity	NPC212891
0.781	Intermediate Similarity	NPC298115
0.7807	Intermediate Similarity	NPC203732
0.7807	Intermediate Similarity	NPC21929
0.7807	Intermediate Similarity	NPC470007
0.7798	Intermediate Similarity	NPC324602
0.7797	Intermediate Similarity	NPC186933
0.7788	Intermediate Similarity	NPC43945
0.7778	Intermediate Similarity	NPC242957
0.7778	Intermediate Similarity	NPC206414
0.7778	Intermediate Similarity	NPC472880
0.7778	Intermediate Similarity	NPC287055
0.7778	Intermediate Similarity	NPC306977
0.7769	Intermediate Similarity	NPC474659
0.7769	Intermediate Similarity	NPC23894
0.7768	Intermediate Similarity	NPC475939
0.7768	Intermediate Similarity	NPC472691
0.7768	Intermediate Similarity	NPC474866
0.7768	Intermediate Similarity	NPC471829
0.776	Intermediate Similarity	NPC294050
0.776	Intermediate Similarity	NPC328997
0.7759	Intermediate Similarity	NPC95126
0.7759	Intermediate Similarity	NPC475002
0.775	Intermediate Similarity	NPC268930
0.7742	Intermediate Similarity	NPC51079
0.7742	Intermediate Similarity	NPC325740
0.7736	Intermediate Similarity	NPC277277
0.7736	Intermediate Similarity	NPC19256
0.7712	Intermediate Similarity	NPC241851
0.7712	Intermediate Similarity	NPC294458
0.7698	Intermediate Similarity	NPC146239
0.7692	Intermediate Similarity	NPC160339
0.7692	Intermediate Similarity	NPC307
0.7674	Intermediate Similarity	NPC471851
0.7667	Intermediate Similarity	NPC158157
0.7664	Intermediate Similarity	NPC125226
0.7652	Intermediate Similarity	NPC211439
0.7647	Intermediate Similarity	NPC228936
0.7647	Intermediate Similarity	NPC221275
0.7642	Intermediate Similarity	NPC144547
0.7642	Intermediate Similarity	NPC418308
0.7638	Intermediate Similarity	NPC72667
0.7638	Intermediate Similarity	NPC316553
0.7636	Intermediate Similarity	NPC156021
0.7619	Intermediate Similarity	NPC69057
0.7619	Intermediate Similarity	NPC470765
0.7615	Intermediate Similarity	NPC58685
0.7611	Intermediate Similarity	NPC19856
0.7603	Intermediate Similarity	NPC45794
0.76	Intermediate Similarity	NPC140118
0.76	Intermediate Similarity	NPC12881
0.7589	Intermediate Similarity	NPC264728
0.7586	Intermediate Similarity	NPC318327
0.7583	Intermediate Similarity	NPC135730
0.7565	Intermediate Similarity	NPC244933
0.7565	Intermediate Similarity	NPC85560
0.7561	Intermediate Similarity	NPC133389
0.7561	Intermediate Similarity	NPC289432
0.7561	Intermediate Similarity	NPC183339
0.7561	Intermediate Similarity	NPC234337
0.7561	Intermediate Similarity	NPC232958
0.7561	Intermediate Similarity	NPC988
0.7559	Intermediate Similarity	NPC254492
0.7559	Intermediate Similarity	NPC71610
0.7559	Intermediate Similarity	NPC473220
0.7559	Intermediate Similarity	NPC470648
0.7559	Intermediate Similarity	NPC470753
0.7557	Intermediate Similarity	NPC78307
0.7557	Intermediate Similarity	NPC203486
0.7557	Intermediate Similarity	NPC310662
0.7547	Intermediate Similarity	NPC153308
0.7547	Intermediate Similarity	NPC267262
0.752	Intermediate Similarity	NPC65627
0.7519	Intermediate Similarity	NPC34414
0.7519	Intermediate Similarity	NPC146647
0.7519	Intermediate Similarity	NPC171460
0.75	Intermediate Similarity	NPC187725
0.75	Intermediate Similarity	NPC103346
0.75	Intermediate Similarity	NPC54647
0.75	Intermediate Similarity	NPC84672
0.75	Intermediate Similarity	NPC176130
0.75	Intermediate Similarity	NPC202225
0.75	Intermediate Similarity	NPC472678
0.75	Intermediate Similarity	NPC274839
0.75	Intermediate Similarity	NPC69424
0.75	Intermediate Similarity	NPC472980
0.75	Intermediate Similarity	NPC141607
0.75	Intermediate Similarity	NPC78364
0.7481	Intermediate Similarity	NPC144257
0.748	Intermediate Similarity	NPC275576
0.7479	Intermediate Similarity	NPC13784
0.7477	Intermediate Similarity	NPC240042
0.7477	Intermediate Similarity	NPC289201
0.7462	Intermediate Similarity	NPC471334
0.7462	Intermediate Similarity	NPC55949
0.7459	Intermediate Similarity	NPC152812
0.7458	Intermediate Similarity	NPC133308
0.7442	Intermediate Similarity	NPC3009

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 NPC470253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	843
0.2-0.3	1216
0.3-0.4	2891
0.4-0.5	2497
0.5-0.6	1246
0.6-0.7	218
0.7-0.8	31
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8899	High Similarity	NPD4141	Clinical (unspecified phase)
0.8654	High Similarity	NPD3495	Discontinued
0.8448	Intermediate Similarity	NPD7009	Phase 2
0.8205	Intermediate Similarity	NPD7610	Discontinued
0.8103	Intermediate Similarity	NPD5951	Approved
0.8095	Intermediate Similarity	NPD7631	Approved
0.8091	Intermediate Similarity	NPD1930	Approved
0.8091	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD1929	Approved
0.8083	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1932	Approved
0.8	Intermediate Similarity	NPD7609	Phase 3
0.8	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD2066	Phase 3
0.7895	Intermediate Similarity	NPD2329	Discontinued
0.7851	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD650	Approved
0.7778	Intermediate Similarity	NPD7094	Approved
0.7778	Intermediate Similarity	NPD6858	Approved
0.7685	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7961	Discontinued
0.7656	Intermediate Similarity	NPD7008	Discontinued
0.7642	Intermediate Similarity	NPD4879	Approved
0.7586	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1088	Approved
0.7391	Intermediate Similarity	NPD1237	Approved
0.7373	Intermediate Similarity	NPD1317	Discontinued
0.7297	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1693	Approved
0.7273	Intermediate Similarity	NPD1508	Approved
0.7248	Intermediate Similarity	NPD1089	Approved
0.7248	Intermediate Similarity	NPD1086	Approved
0.7248	Intermediate Similarity	NPD1090	Approved
0.7244	Intermediate Similarity	NPD4878	Approved
0.7231	Intermediate Similarity	NPD7084	Phase 3
0.7156	Intermediate Similarity	NPD800	Approved
0.7154	Intermediate Similarity	NPD3317	Approved
0.7143	Intermediate Similarity	NPD2932	Approved
0.708	Intermediate Similarity	NPD1843	Approved
0.708	Intermediate Similarity	NPD1989	Approved
0.7073	Intermediate Similarity	NPD2629	Approved
0.7048	Intermediate Similarity	NPD942	Approved
0.7027	Intermediate Similarity	NPD1239	Approved
0.7021	Intermediate Similarity	NPD7236	Approved
0.7018	Intermediate Similarity	NPD1564	Approved
0.7018	Intermediate Similarity	NPD1565	Approved
0.7018	Intermediate Similarity	NPD1566	Phase 3
0.7009	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6647	Phase 2
0.7008	Intermediate Similarity	NPD2345	Approved
0.7008	Intermediate Similarity	NPD3019	Approved
0.7	Intermediate Similarity	NPD7003	Approved
0.6992	Remote Similarity	NPD6010	Discontinued
0.6991	Remote Similarity	NPD6049	Phase 2
0.6991	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1087	Approved
0.6967	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5909	Discontinued
0.694	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7055	Discontinued
0.6897	Remote Similarity	NPD7239	Suspended
0.6885	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4199	Phase 3
0.686	Remote Similarity	NPD2182	Approved
0.6847	Remote Similarity	NPD5347	Phase 2
0.6847	Remote Similarity	NPD5346	Phase 2
0.6818	Remote Similarity	NPD1470	Approved
0.6797	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5157	Phase 1
0.6794	Remote Similarity	NPD5159	Phase 2
0.6786	Remote Similarity	NPD3673	Approved
0.6786	Remote Similarity	NPD3672	Approved
0.6769	Remote Similarity	NPD1201	Approved
0.6769	Remote Similarity	NPD6287	Discontinued
0.6767	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6273	Approved
0.6754	Remote Similarity	NPD1563	Approved
0.6744	Remote Similarity	NPD5836	Discontinued
0.6742	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD226	Approved
0.672	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD3972	Approved
0.6713	Remote Similarity	NPD7295	Approved
0.6693	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD3026	Approved
0.6692	Remote Similarity	NPD3023	Approved
0.6691	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD4793	Discontinued
0.6667	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD164	Approved
0.6667	Remote Similarity	NPD3024	Approved
0.6643	Remote Similarity	NPD8166	Discontinued
0.6642	Remote Similarity	NPD7715	Approved
0.6642	Remote Similarity	NPD7714	Approved
0.6642	Remote Similarity	NPD7713	Phase 3
0.6639	Remote Similarity	NPD2193	Phase 2
0.6639	Remote Similarity	NPD2648	Phase 3
0.6636	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7458	Discontinued
0.6621	Remote Similarity	NPD8165	Discontinued
0.6618	Remote Similarity	NPD6966	Discovery
0.6617	Remote Similarity	NPD1876	Approved
0.6606	Remote Similarity	NPD9491	Approved
0.6596	Remote Similarity	NPD5405	Approved
0.6596	Remote Similarity	NPD5408	Approved
0.6596	Remote Similarity	NPD5404	Approved
0.6596	Remote Similarity	NPD5406	Approved
0.6583	Remote Similarity	NPD5765	Approved
0.6577	Remote Similarity	NPD5279	Phase 3
0.6557	Remote Similarity	NPD6685	Approved
0.6555	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2346	Discontinued
0.6545	Remote Similarity	NPD3665	Phase 1
0.6545	Remote Similarity	NPD3133	Approved
0.6545	Remote Similarity	NPD3666	Approved
0.6541	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1245	Approved
0.6525	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6663	Approved
0.6519	Remote Similarity	NPD2798	Approved
0.6519	Remote Similarity	NPD4980	Approved
0.6515	Remote Similarity	NPD5618	Discontinued
0.6512	Remote Similarity	NPD6065	Approved
0.651	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2196	Discontinued
0.6493	Remote Similarity	NPD1283	Approved
0.6491	Remote Similarity	NPD9256	Approved
0.6491	Remote Similarity	NPD9258	Approved
0.6486	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4198	Discontinued
0.648	Remote Similarity	NPD3643	Approved
0.648	Remote Similarity	NPD3642	Approved
0.648	Remote Similarity	NPD3644	Approved
0.6475	Remote Similarity	NPD1018	Approved
0.6475	Remote Similarity	NPD5048	Discontinued
0.6471	Remote Similarity	NPD7798	Approved
0.6471	Remote Similarity	NPD7057	Phase 3
0.6471	Remote Similarity	NPD1238	Approved
0.6471	Remote Similarity	NPD5736	Approved
0.6471	Remote Similarity	NPD7058	Phase 2
0.6466	Remote Similarity	NPD1202	Approved
0.6463	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD3091	Approved
0.6458	Remote Similarity	NPD7082	Approved
0.6455	Remote Similarity	NPD3971	Phase 1
0.6449	Remote Similarity	NPD227	Approved
0.6449	Remote Similarity	NPD225	Approved
0.6438	Remote Similarity	NPD3300	Phase 2
0.6435	Remote Similarity	NPD6079	Approved
0.6434	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3618	Phase 1
0.6414	Remote Similarity	NPD7259	Approved
0.6414	Remote Similarity	NPD4628	Phase 3
0.6412	Remote Similarity	NPD1651	Approved
0.641	Remote Similarity	NPD4094	Approved
0.641	Remote Similarity	NPD4814	Discontinued
0.6406	Remote Similarity	NPD4766	Approved
0.6406	Remote Similarity	NPD1246	Approved
0.64	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD9495	Approved
0.6383	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3095	Discontinued
0.6364	Remote Similarity	NPD3667	Approved
0.6356	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD7741	Discontinued
0.633	Remote Similarity	NPD4695	Discontinued
0.6328	Remote Similarity	NPD2652	Approved
0.6328	Remote Similarity	NPD2650	Approved
0.6325	Remote Similarity	NPD3719	Approved
0.6325	Remote Similarity	NPD3718	Approved
0.6311	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4655	Approved
0.6303	Remote Similarity	NPD4657	Approved
0.6301	Remote Similarity	NPD7487	Discontinued
0.6294	Remote Similarity	NPD7305	Phase 1
0.6294	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD2799	Discontinued
0.6293	Remote Similarity	NPD7515	Phase 2
0.6288	Remote Similarity	NPD5981	Approved
0.6284	Remote Similarity	NPD7390	Discontinued
0.6283	Remote Similarity	NPD5280	Approved
0.6283	Remote Similarity	NPD9259	Approved
0.6283	Remote Similarity	NPD5690	Phase 2
0.6283	Remote Similarity	NPD9257	Approved
0.6283	Remote Similarity	NPD4694	Approved
0.6271	Remote Similarity	NPD5210	Approved
0.6271	Remote Similarity	NPD4629	Approved
0.627	Remote Similarity	NPD664	Approved
0.6269	Remote Similarity	NPD1281	Approved
0.6269	Remote Similarity	NPD3092	Approved
0.6261	Remote Similarity	NPD4753	Phase 2
0.6261	Remote Similarity	NPD5328	Approved
0.6261	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD2754	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data