NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	381.03
Volume:	337.47
LogP:	0.49
LogD:	-0.132
LogS:	-3.135
# Rotatable Bonds:	5
TPSA:	145.58
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.302
Synthetic Accessibility Score:	4.038
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.111
MDCK Permeability:	1.0582181857898831e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.177

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	98.1506576538086%
Volume Distribution (VD):	0.371
Pgp-substrate:	1.0442863702774048%

ADMET: Metabolism

CYP1A2-inhibitor:	0.591
CYP1A2-substrate:	0.207
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.809
CYP2D6-substrate:	0.451
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.083

ADMET: Excretion

Clearance (CL):	1.05
Half-life (T1/2):	0.463

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.973
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.217
Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.562
Carcinogencity:	0.972
Eye Corrosion:	0.003
Eye Irritation:	0.389
Respiratory Toxicity:	0.886

Download Data

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

Natural Product: NPC477797

Natural Product ID:	NPC477797
*Common Name:**	sodium;[(E)-2-[2-[(3,4-dihydroxyphenyl)-hydroxymethyl]-1,3-benzodioxol-5-yl]ethenyl] sulfate
IUPAC Name:	sodium;[(E)-2-[2-[(3,4-dihydroxyphenyl)-hydroxymethyl]-1,3-benzodioxol-5-yl]ethenyl] sulfate
Synonyms:
Standard InCHIKey:	HTPPCRGQTKJFTP-IPZCTEOASA-M
Standard InCHI:	InChI=1S/C16H14O9S.Na/c17-11-3-2-10(8-12(11)18)15(19)16-24-13-4-1-9(7-14(13)25-16)5-6-23-26(20,21)22;/h1-8,15-19H,(H,20,21,22);/q;+1/p-1/b6-5+;
SMILES:	C1=CC2=C(C=C1/C=C/OS(=O)(=O)[O-])OC(O2)C(C3=CC(=C(C=C3)O)O)O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	24878739
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	Vanuatu islands	n.a.	PMID[10924170]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277766]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640526]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18990572]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326327]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	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
IC50	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	123.9	ug/ml	PMID[18407691]
NPT2	Others	Unspecified		IC50	>	200	ug/ml	PMID[18407691]

☑ 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 NPC477797 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	414
0.1-0.2	1838
0.2-0.3	5565
0.3-0.4	12276
0.4-0.5	5301
0.5-0.6	6451
0.6-0.7	7306
0.7-0.8	2897
0.8-0.85	530
0.85-0.9	112
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477798
0.927	High Similarity	NPC477800
0.927	High Similarity	NPC477794
0.927	High Similarity	NPC477799
0.9118	High Similarity	NPC138738
0.9118	High Similarity	NPC470413
0.9065	High Similarity	NPC46092
0.9065	High Similarity	NPC470950
0.9065	High Similarity	NPC185307
0.9037	High Similarity	NPC470881
0.9023	High Similarity	NPC477804
0.9	High Similarity	NPC283995
0.9	High Similarity	NPC470235
0.9	High Similarity	NPC129417
0.8993	High Similarity	NPC476356
0.8986	High Similarity	NPC106944
0.8971	High Similarity	NPC184938
0.8971	High Similarity	NPC101624
0.8963	High Similarity	NPC25821
0.8963	High Similarity	NPC6836
0.8955	High Similarity	NPC65942
0.8955	High Similarity	NPC248307
0.8936	High Similarity	NPC18979
0.8936	High Similarity	NPC469586
0.8936	High Similarity	NPC22150
0.8936	High Similarity	NPC38041
0.8936	High Similarity	NPC279298
0.8921	High Similarity	NPC472711
0.8921	High Similarity	NPC469661
0.8905	High Similarity	NPC25695
0.8905	High Similarity	NPC177035
0.8905	High Similarity	NPC52277
0.8905	High Similarity	NPC199459
0.8905	High Similarity	NPC172818
0.8897	High Similarity	NPC476411
0.8897	High Similarity	NPC187194
0.8889	High Similarity	NPC252833
0.8889	High Similarity	NPC471505
0.8889	High Similarity	NPC106739
0.8881	High Similarity	NPC80600
0.8881	High Similarity	NPC472024
0.8873	High Similarity	NPC112861
0.8864	High Similarity	NPC178284
0.8864	High Similarity	NPC58607
0.8864	High Similarity	NPC191037
0.8857	High Similarity	NPC469559
0.8857	High Similarity	NPC253878
0.8857	High Similarity	NPC189115
0.8841	High Similarity	NPC59324
0.8841	High Similarity	NPC65530
0.8832	High Similarity	NPC135777
0.8832	High Similarity	NPC142547
0.8815	High Similarity	NPC9912
0.8811	High Similarity	NPC39657
0.8811	High Similarity	NPC114505
0.8811	High Similarity	NPC275284
0.8811	High Similarity	NPC213074
0.8811	High Similarity	NPC15956
0.8811	High Similarity	NPC31325
0.8811	High Similarity	NPC193473
0.8811	High Similarity	NPC224674
0.8806	High Similarity	NPC26653
0.8806	High Similarity	NPC270849
0.8806	High Similarity	NPC307110
0.8806	High Similarity	NPC166040
0.8806	High Similarity	NPC248355
0.8797	High Similarity	NPC292056
0.8797	High Similarity	NPC118787
0.8797	High Similarity	NPC147821
0.8797	High Similarity	NPC183181
0.8797	High Similarity	NPC163332
0.8797	High Similarity	NPC111247
0.8797	High Similarity	NPC319625
0.8797	High Similarity	NPC41706
0.8794	High Similarity	NPC477898
0.8788	High Similarity	NPC194519
0.8786	High Similarity	NPC471414
0.8777	High Similarity	NPC98777
0.8777	High Similarity	NPC212770
0.8768	High Similarity	NPC203230
0.8768	High Similarity	NPC242028
0.8759	High Similarity	NPC35731
0.8741	High Similarity	NPC173308
0.8741	High Similarity	NPC275950
0.8741	High Similarity	NPC181079
0.8732	High Similarity	NPC25292
0.8732	High Similarity	NPC84181
0.8732	High Similarity	NPC473045
0.8731	High Similarity	NPC302378
0.8731	High Similarity	NPC72529
0.8723	High Similarity	NPC475084
0.8723	High Similarity	NPC302506
0.8723	High Similarity	NPC246947
0.8712	High Similarity	NPC109822
0.8712	High Similarity	NPC94276
0.869	High Similarity	NPC55158
0.869	High Similarity	NPC51328
0.869	High Similarity	NPC286235
0.8686	High Similarity	NPC169973
0.8676	High Similarity	NPC476345
0.8676	High Similarity	NPC166168
0.8671	High Similarity	NPC475096
0.8671	High Similarity	NPC476301
0.8671	High Similarity	NPC43508
0.8667	High Similarity	NPC86030
0.8667	High Similarity	NPC5851
0.8662	High Similarity	NPC252169
0.8662	High Similarity	NPC473044
0.8662	High Similarity	NPC478239
0.8652	High Similarity	NPC186406
0.8643	High Similarity	NPC156376
0.8643	High Similarity	NPC292487
0.8643	High Similarity	NPC123526
0.8643	High Similarity	NPC88640
0.8643	High Similarity	NPC193666
0.8633	High Similarity	NPC77861
0.863	High Similarity	NPC475224
0.863	High Similarity	NPC98624
0.8623	High Similarity	NPC13745
0.8623	High Similarity	NPC251981
0.8623	High Similarity	NPC107478
0.8623	High Similarity	NPC48863
0.8623	High Similarity	NPC87696
0.8621	High Similarity	NPC304048
0.8621	High Similarity	NPC248132
0.8621	High Similarity	NPC226153
0.8621	High Similarity	NPC130449
0.8613	High Similarity	NPC219671
0.8613	High Similarity	NPC184447
0.8613	High Similarity	NPC16208
0.8613	High Similarity	NPC160991
0.8613	High Similarity	NPC147616
0.8613	High Similarity	NPC7903
0.8613	High Similarity	NPC259742
0.8613	High Similarity	NPC104077
0.8613	High Similarity	NPC35932
0.8611	High Similarity	NPC125755
0.8611	High Similarity	NPC190714
0.8611	High Similarity	NPC99515
0.8603	High Similarity	NPC257582
0.8603	High Similarity	NPC77040
0.8603	High Similarity	NPC241522
0.8603	High Similarity	NPC174495
0.8603	High Similarity	NPC64201
0.8603	High Similarity	NPC145305
0.8603	High Similarity	NPC242807
0.8603	High Similarity	NPC187998
0.8603	High Similarity	NPC42300
0.8603	High Similarity	NPC153739
0.8603	High Similarity	NPC92164
0.8601	High Similarity	NPC471063
0.8601	High Similarity	NPC473046
0.8601	High Similarity	NPC471667
0.8601	High Similarity	NPC472712
0.8601	High Similarity	NPC217635
0.8601	High Similarity	NPC76176
0.8601	High Similarity	NPC79429
0.8601	High Similarity	NPC138227
0.8601	High Similarity	NPC472713
0.8601	High Similarity	NPC187774
0.8601	High Similarity	NPC168579
0.8601	High Similarity	NPC232228
0.8601	High Similarity	NPC179521
0.8601	High Similarity	NPC469313
0.8601	High Similarity	NPC118385
0.8593	High Similarity	NPC11258
0.8593	High Similarity	NPC128208
0.8593	High Similarity	NPC129570
0.8593	High Similarity	NPC282703
0.8593	High Similarity	NPC45774
0.8593	High Similarity	NPC21867
0.8593	High Similarity	NPC184733
0.8592	High Similarity	NPC60249
0.8592	High Similarity	NPC48309
0.8592	High Similarity	NPC157816
0.8592	High Similarity	NPC140502
0.8571	High Similarity	NPC48990
0.8571	High Similarity	NPC304152
0.8571	High Similarity	NPC195196
0.8571	High Similarity	NPC114901
0.8571	High Similarity	NPC293701
0.8571	High Similarity	NPC474039
0.8561	High Similarity	NPC71090
0.8561	High Similarity	NPC18576
0.8552	High Similarity	NPC227902
0.8551	High Similarity	NPC132895
0.8551	High Similarity	NPC215833
0.8551	High Similarity	NPC69513
0.8551	High Similarity	NPC49074
0.8542	High Similarity	NPC161700
0.8542	High Similarity	NPC277867
0.854	High Similarity	NPC472597
0.854	High Similarity	NPC277804
0.8531	High Similarity	NPC278961
0.8531	High Similarity	NPC113680
0.8531	High Similarity	NPC37793
0.8531	High Similarity	NPC81638
0.8529	High Similarity	NPC475875
0.8521	High Similarity	NPC76871
0.8521	High Similarity	NPC471908

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 NPC477797 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	920
0.2-0.3	2077
0.3-0.4	2755
0.4-0.5	1580
0.5-0.6	927
0.6-0.7	486
0.7-0.8	56
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD3027	Phase 3
0.8214	Intermediate Similarity	NPD1613	Approved
0.8214	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD3705	Approved
0.8	Intermediate Similarity	NPD7266	Discontinued
0.7985	Intermediate Similarity	NPD1357	Approved
0.7947	Intermediate Similarity	NPD1653	Approved
0.7941	Intermediate Similarity	NPD1091	Approved
0.7929	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3818	Discontinued
0.7786	Intermediate Similarity	NPD228	Approved
0.7692	Intermediate Similarity	NPD2977	Approved
0.7692	Intermediate Similarity	NPD2978	Approved
0.7651	Intermediate Similarity	NPD6674	Discontinued
0.761	Intermediate Similarity	NPD6234	Discontinued
0.7606	Intermediate Similarity	NPD2861	Phase 2
0.7586	Intermediate Similarity	NPD1558	Phase 1
0.7566	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7054	Approved
0.7516	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD7472	Approved
0.7515	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD5058	Phase 3
0.7484	Intermediate Similarity	NPD4965	Approved
0.7484	Intermediate Similarity	NPD4966	Approved
0.7484	Intermediate Similarity	NPD4967	Phase 2
0.7447	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5283	Phase 1
0.7407	Intermediate Similarity	NPD7199	Phase 2
0.7381	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6797	Phase 2
0.7347	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3620	Phase 2
0.7333	Intermediate Similarity	NPD7843	Approved
0.7321	Intermediate Similarity	NPD7251	Discontinued
0.7303	Intermediate Similarity	NPD4237	Approved
0.7303	Intermediate Similarity	NPD4236	Phase 3
0.7299	Intermediate Similarity	NPD7157	Approved
0.7296	Intermediate Similarity	NPD1934	Approved
0.7293	Intermediate Similarity	NPD2684	Approved
0.7285	Intermediate Similarity	NPD1375	Discontinued
0.7278	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD968	Approved
0.7267	Intermediate Similarity	NPD5588	Approved
0.7266	Intermediate Similarity	NPD1548	Phase 1
0.723	Intermediate Similarity	NPD4060	Phase 1
0.7222	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7685	Pre-registration
0.7212	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2982	Phase 2
0.7203	Intermediate Similarity	NPD2983	Phase 2
0.719	Intermediate Similarity	NPD3060	Approved
0.719	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1610	Phase 2
0.7162	Intermediate Similarity	NPD4062	Phase 3
0.716	Intermediate Similarity	NPD3882	Suspended
0.716	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8455	Phase 2
0.7133	Intermediate Similarity	NPD2981	Phase 2
0.7123	Intermediate Similarity	NPD3018	Phase 2
0.7118	Intermediate Similarity	NPD6559	Discontinued
0.7111	Intermediate Similarity	NPD3022	Approved
0.7111	Intermediate Similarity	NPD3021	Approved
0.7107	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6190	Approved
0.709	Intermediate Similarity	NPD290	Approved
0.7086	Intermediate Similarity	NPD4536	Approved
0.7086	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4538	Approved
0.7078	Intermediate Similarity	NPD4162	Approved
0.7075	Intermediate Similarity	NPD4908	Phase 1
0.707	Intermediate Similarity	NPD4123	Phase 3
0.7067	Intermediate Similarity	NPD4340	Discontinued
0.7066	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6166	Phase 2
0.7066	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3687	Approved
0.7044	Intermediate Similarity	NPD3686	Approved
0.7042	Intermediate Similarity	NPD5846	Approved
0.7042	Intermediate Similarity	NPD6516	Phase 2
0.7039	Intermediate Similarity	NPD5960	Phase 3
0.7037	Intermediate Similarity	NPD5773	Approved
0.7037	Intermediate Similarity	NPD5772	Approved
0.7037	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2801	Approved
0.7032	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4110	Phase 3
0.7032	Intermediate Similarity	NPD4628	Phase 3
0.7021	Intermediate Similarity	NPD1182	Approved
0.7018	Intermediate Similarity	NPD7240	Approved
0.7014	Intermediate Similarity	NPD2231	Phase 2
0.7014	Intermediate Similarity	NPD2235	Phase 2
0.7006	Intermediate Similarity	NPD1511	Approved
0.6987	Remote Similarity	NPD2677	Approved
0.6981	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.697	Remote Similarity	NPD291	Approved
0.6959	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6355	Discontinued
0.6954	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5735	Approved
0.695	Remote Similarity	NPD5536	Phase 2
0.6948	Remote Similarity	NPD5762	Approved
0.6948	Remote Similarity	NPD5763	Approved
0.6948	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6584	Phase 3
0.6933	Remote Similarity	NPD6233	Phase 2
0.6933	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6671	Approved
0.6923	Remote Similarity	NPD5125	Phase 3
0.6923	Remote Similarity	NPD6331	Phase 2
0.6923	Remote Similarity	NPD5126	Approved
0.6918	Remote Similarity	NPD8651	Approved
0.6918	Remote Similarity	NPD1512	Approved
0.6913	Remote Similarity	NPD7095	Approved
0.6909	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5604	Discontinued
0.6908	Remote Similarity	NPD6653	Approved
0.6897	Remote Similarity	NPD1840	Phase 2
0.689	Remote Similarity	NPD3817	Phase 2
0.6867	Remote Similarity	NPD6798	Discontinued
0.6863	Remote Similarity	NPD7097	Phase 1
0.6861	Remote Similarity	NPD556	Approved
0.6852	Remote Similarity	NPD4675	Approved
0.6852	Remote Similarity	NPD4678	Approved
0.6849	Remote Similarity	NPD3685	Discontinued
0.6842	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3657	Discovery
0.6839	Remote Similarity	NPD3540	Phase 1
0.6828	Remote Similarity	NPD1535	Discovery
0.6821	Remote Similarity	NPD2674	Phase 3
0.6815	Remote Similarity	NPD3892	Phase 2
0.6813	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD9381	Approved
0.6806	Remote Similarity	NPD9384	Approved
0.6792	Remote Similarity	NPD1774	Approved
0.6788	Remote Similarity	NPD2563	Approved
0.6788	Remote Similarity	NPD2560	Approved
0.6786	Remote Similarity	NPD8127	Discontinued
0.6783	Remote Similarity	NPD1894	Discontinued
0.6781	Remote Similarity	NPD1481	Phase 2
0.6781	Remote Similarity	NPD1608	Approved
0.6779	Remote Similarity	NPD9494	Approved
0.6776	Remote Similarity	NPD4140	Approved
0.6776	Remote Similarity	NPD3059	Approved
0.6776	Remote Similarity	NPD3061	Approved
0.6776	Remote Similarity	NPD3062	Approved
0.6774	Remote Similarity	NPD3539	Phase 1
0.6774	Remote Similarity	NPD2161	Phase 2
0.6765	Remote Similarity	NPD2489	Approved
0.6765	Remote Similarity	NPD27	Approved
0.6763	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3496	Discontinued
0.6757	Remote Similarity	NPD7680	Approved
0.6755	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1652	Phase 2
0.675	Remote Similarity	NPD3536	Discontinued
0.6746	Remote Similarity	NPD3787	Discontinued
0.6735	Remote Similarity	NPD6582	Phase 2
0.6735	Remote Similarity	NPD6583	Phase 3
0.6735	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD1465	Phase 2
0.6721	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD5535	Approved
0.6712	Remote Similarity	NPD422	Phase 1
0.6711	Remote Similarity	NPD558	Phase 2
0.6711	Remote Similarity	NPD554	Clinical (unspecified phase)
0.671	Remote Similarity	NPD4108	Discontinued
0.671	Remote Similarity	NPD7033	Discontinued
0.6709	Remote Similarity	NPD4535	Phase 3
0.6706	Remote Similarity	NPD2970	Approved
0.6706	Remote Similarity	NPD2969	Approved
0.6705	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3180	Approved
0.6689	Remote Similarity	NPD3179	Approved
0.6689	Remote Similarity	NPD6696	Suspended
0.6689	Remote Similarity	NPD4625	Phase 3
0.6688	Remote Similarity	NPD3054	Approved
0.6688	Remote Similarity	NPD5314	Approved
0.6688	Remote Similarity	NPD3052	Approved
0.6686	Remote Similarity	NPD3751	Discontinued
0.6685	Remote Similarity	NPD6842	Approved
0.6685	Remote Similarity	NPD6843	Phase 3
0.6685	Remote Similarity	NPD6841	Approved
0.6667	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2122	Discontinued
0.6667	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7007	Discovery
0.6667	Remote Similarity	NPD6032	Approved
0.6667	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5241	Discontinued
0.6648	Remote Similarity	NPD8313	Approved
0.6648	Remote Similarity	NPD8312	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