NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	452.16
Volume:	441.619
LogP:	3.744
LogD:	2.352
LogS:	-4.093
# Rotatable Bonds:	6
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.566
Synthetic Accessibility Score:	5.452
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.228
MDCK Permeability:	1.8763155821943656e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.114
Human Intestinal Absorption (HIA):	0.124
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.966
Plasma Protein Binding (PPB):	77.07022094726562%
Volume Distribution (VD):	0.883
Pgp-substrate:	15.30972671508789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.431
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.742
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.272
CYP3A4-substrate:	0.331

ADMET: Excretion

Clearance (CL):	4.293
Half-life (T1/2):	0.171

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.933
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.866
Maximum Recommended Daily Dose:	0.139
Skin Sensitization:	0.782
Carcinogencity:	0.935
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC476815

Natural Product ID:	NPC476815
*Common Name:**	(6aS,9S,9aS)-5-chloro-8-hydroxy-8-(3-hydroxybutan-2-yl)-6a-methyl-3-[(E,3S)-3-methylpent-1-enyl]-6-oxo-9,9a-dihydrofuro[2,3-h]isochromene-9-carboxylic acid
IUPAC Name:	(6aS,9S,9aS)-5-chloro-8-hydroxy-8-(3-hydroxybutan-2-yl)-6a-methyl-3-[(E,3S)-3-methylpent-1-enyl]-6-oxo-9,9a-dihydrofuro[2,3-h]isochromene-9-carboxylic acid
Synonyms:	Chaetoviridin B
Standard InCHIKey:	TVZGDEYWRLMKPX-POQNFFFHSA-N
Standard InCHI:	InChI=1S/C23H29ClO7/c1-6-11(2)7-8-14-9-15-16(10-30-14)17-18(21(27)28)23(29,12(3)13(4)25)31-22(17,5)20(26)19(15)24/h7-13,17-18,25,29H,6H2,1-5H3,(H,27,28)/b8-7+/t11-,12?,13?,17+,18+,22-,23?/m0/s1
SMILES:	CC[C@H](C)/C=C/C1=CC2=C(C(=O)[C@@]3([C@H](C2=CO1)[C@@H](C(O3)(C(C)C(C)O)O)C(=O)O)C)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	56676698
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	1.23	ug/ml	PMID[21548578]
NPT2527	Organism	Pythium ultimum	Pythium ultimum	MIC	=	33.3	ug/ml	PMID[21548578]

☑ 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 NPC476815 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	223
0.1-0.2	1244
0.2-0.3	4240
0.3-0.4	8534
0.4-0.5	15368
0.5-0.6	9115
0.6-0.7	3626
0.7-0.8	331
0.8-0.85	11
0.85-0.9	0
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC31641
0.9554	High Similarity	NPC245320
0.9469	High Similarity	NPC473145
0.9204	High Similarity	NPC243298
0.8636	High Similarity	NPC297281
0.8636	High Similarity	NPC473144
0.8407	Intermediate Similarity	NPC232969
0.8407	Intermediate Similarity	NPC199107
0.8304	Intermediate Similarity	NPC271059
0.8304	Intermediate Similarity	NPC25666
0.8261	Intermediate Similarity	NPC23497
0.823	Intermediate Similarity	NPC272528
0.8198	Intermediate Similarity	NPC215253
0.8198	Intermediate Similarity	NPC185253
0.8108	Intermediate Similarity	NPC166770
0.8018	Intermediate Similarity	NPC134083
0.7983	Intermediate Similarity	NPC326264
0.7965	Intermediate Similarity	NPC469851
0.7899	Intermediate Similarity	NPC66108
0.7845	Intermediate Similarity	NPC469852
0.7838	Intermediate Similarity	NPC31021
0.7833	Intermediate Similarity	NPC321496
0.7807	Intermediate Similarity	NPC224172
0.7778	Intermediate Similarity	NPC469853
0.7686	Intermediate Similarity	NPC474271
0.7661	Intermediate Similarity	NPC268958
0.7652	Intermediate Similarity	NPC244456
0.7652	Intermediate Similarity	NPC469657
0.7647	Intermediate Similarity	NPC38154
0.7607	Intermediate Similarity	NPC472756
0.7589	Intermediate Similarity	NPC143210
0.7586	Intermediate Similarity	NPC235369
0.7583	Intermediate Similarity	NPC478209
0.7561	Intermediate Similarity	NPC270478
0.7542	Intermediate Similarity	NPC469607
0.7541	Intermediate Similarity	NPC469454
0.7541	Intermediate Similarity	NPC469496
0.7541	Intermediate Similarity	NPC469463
0.7522	Intermediate Similarity	NPC12727
0.7521	Intermediate Similarity	NPC475871
0.7521	Intermediate Similarity	NPC472747
0.7521	Intermediate Similarity	NPC179798
0.7521	Intermediate Similarity	NPC472750
0.7521	Intermediate Similarity	NPC320294
0.7521	Intermediate Similarity	NPC304180
0.7521	Intermediate Similarity	NPC475945
0.752	Intermediate Similarity	NPC476107
0.7519	Intermediate Similarity	NPC476008
0.75	Intermediate Similarity	NPC472753
0.75	Intermediate Similarity	NPC24651
0.748	Intermediate Similarity	NPC287236
0.748	Intermediate Similarity	NPC312833
0.7458	Intermediate Similarity	NPC472748
0.7442	Intermediate Similarity	NPC477745
0.744	Intermediate Similarity	NPC284707
0.744	Intermediate Similarity	NPC21326
0.7438	Intermediate Similarity	NPC89408
0.7438	Intermediate Similarity	NPC5103
0.7438	Intermediate Similarity	NPC206595
0.7436	Intermediate Similarity	NPC303653
0.7436	Intermediate Similarity	NPC273005
0.7436	Intermediate Similarity	NPC469606
0.7436	Intermediate Similarity	NPC291500
0.7436	Intermediate Similarity	NPC197835
0.7436	Intermediate Similarity	NPC472754
0.7436	Intermediate Similarity	NPC474747
0.7436	Intermediate Similarity	NPC31058
0.7436	Intermediate Similarity	NPC140591
0.7436	Intermediate Similarity	NPC189609
0.7422	Intermediate Similarity	NPC18945
0.7422	Intermediate Similarity	NPC105926
0.7422	Intermediate Similarity	NPC91693
0.7422	Intermediate Similarity	NPC265557
0.7417	Intermediate Similarity	NPC327106
0.7417	Intermediate Similarity	NPC322903
0.7411	Intermediate Similarity	NPC166110
0.7411	Intermediate Similarity	NPC32552
0.7405	Intermediate Similarity	NPC221414
0.7402	Intermediate Similarity	NPC471999
0.7402	Intermediate Similarity	NPC472000
0.7398	Intermediate Similarity	NPC478212
0.7398	Intermediate Similarity	NPC56448
0.7395	Intermediate Similarity	NPC472751
0.7395	Intermediate Similarity	NPC472645
0.7395	Intermediate Similarity	NPC472749
0.7395	Intermediate Similarity	NPC478208
0.7381	Intermediate Similarity	NPC158963
0.7373	Intermediate Similarity	NPC475873
0.7368	Intermediate Similarity	NPC168879
0.7364	Intermediate Similarity	NPC476729
0.7364	Intermediate Similarity	NPC470922
0.736	Intermediate Similarity	NPC471145
0.736	Intermediate Similarity	NPC98249
0.736	Intermediate Similarity	NPC469684
0.736	Intermediate Similarity	NPC53396
0.736	Intermediate Similarity	NPC23046
0.7355	Intermediate Similarity	NPC220705
0.735	Intermediate Similarity	NPC476270
0.735	Intermediate Similarity	NPC474742
0.735	Intermediate Similarity	NPC472643
0.7345	Intermediate Similarity	NPC475302
0.7345	Intermediate Similarity	NPC248193
0.7333	Intermediate Similarity	NPC266514
0.7321	Intermediate Similarity	NPC224270
0.7311	Intermediate Similarity	NPC474741
0.7293	Intermediate Similarity	NPC470185
0.7288	Intermediate Similarity	NPC149371
0.7287	Intermediate Similarity	NPC67251
0.728	Intermediate Similarity	NPC478216
0.7279	Intermediate Similarity	NPC596
0.7273	Intermediate Similarity	NPC476479
0.7273	Intermediate Similarity	NPC203795
0.7273	Intermediate Similarity	NPC476851
0.7265	Intermediate Similarity	NPC54705
0.7265	Intermediate Similarity	NPC472644
0.7259	Intermediate Similarity	NPC262813
0.7258	Intermediate Similarity	NPC25909
0.7258	Intermediate Similarity	NPC159333
0.7257	Intermediate Similarity	NPC193396
0.7257	Intermediate Similarity	NPC32944
0.725	Intermediate Similarity	NPC85529
0.725	Intermediate Similarity	NPC477125
0.725	Intermediate Similarity	NPC32006
0.725	Intermediate Similarity	NPC34768
0.7244	Intermediate Similarity	NPC472933
0.7241	Intermediate Similarity	NPC208094
0.7236	Intermediate Similarity	NPC317107
0.7232	Intermediate Similarity	NPC142159
0.7232	Intermediate Similarity	NPC95364
0.7227	Intermediate Similarity	NPC469980
0.7227	Intermediate Similarity	NPC118902
0.7227	Intermediate Similarity	NPC104161
0.7227	Intermediate Similarity	NPC320154
0.7227	Intermediate Similarity	NPC472755
0.7222	Intermediate Similarity	NPC239273
0.7222	Intermediate Similarity	NPC478204
0.7218	Intermediate Similarity	NPC476862
0.7218	Intermediate Similarity	NPC476852
0.7218	Intermediate Similarity	NPC476863
0.7217	Intermediate Similarity	NPC474947
0.7217	Intermediate Similarity	NPC295347
0.7213	Intermediate Similarity	NPC478210
0.7213	Intermediate Similarity	NPC137911
0.7213	Intermediate Similarity	NPC228477
0.7206	Intermediate Similarity	NPC190065
0.7206	Intermediate Similarity	NPC471089
0.7206	Intermediate Similarity	NPC251998
0.7206	Intermediate Similarity	NPC243014
0.7206	Intermediate Similarity	NPC141215
0.7203	Intermediate Similarity	NPC185141
0.7203	Intermediate Similarity	NPC110443
0.7203	Intermediate Similarity	NPC128733
0.7203	Intermediate Similarity	NPC46998
0.7203	Intermediate Similarity	NPC207885
0.7203	Intermediate Similarity	NPC133907
0.7203	Intermediate Similarity	NPC201718
0.7203	Intermediate Similarity	NPC47880
0.7203	Intermediate Similarity	NPC473384
0.72	Intermediate Similarity	NPC261330
0.7197	Intermediate Similarity	NPC476859
0.7188	Intermediate Similarity	NPC109607
0.7188	Intermediate Similarity	NPC107338
0.7188	Intermediate Similarity	NPC478051
0.7185	Intermediate Similarity	NPC242486
0.7185	Intermediate Similarity	NPC475500
0.7185	Intermediate Similarity	NPC475154
0.7185	Intermediate Similarity	NPC100017
0.7185	Intermediate Similarity	NPC471136
0.7185	Intermediate Similarity	NPC15215
0.7185	Intermediate Similarity	NPC182266
0.7185	Intermediate Similarity	NPC471137
0.7185	Intermediate Similarity	NPC473548
0.7185	Intermediate Similarity	NPC223356
0.7179	Intermediate Similarity	NPC35717
0.7179	Intermediate Similarity	NPC54843
0.7177	Intermediate Similarity	NPC317687
0.7167	Intermediate Similarity	NPC258532
0.7167	Intermediate Similarity	NPC474898
0.7165	Intermediate Similarity	NPC297179
0.7165	Intermediate Similarity	NPC478205
0.7165	Intermediate Similarity	NPC108581
0.7165	Intermediate Similarity	NPC478206
0.7165	Intermediate Similarity	NPC17772
0.7164	Intermediate Similarity	NPC102316
0.7155	Intermediate Similarity	NPC476275
0.7155	Intermediate Similarity	NPC172998
0.7155	Intermediate Similarity	NPC301596
0.7155	Intermediate Similarity	NPC299396
0.7155	Intermediate Similarity	NPC318082
0.7154	Intermediate Similarity	NPC235014
0.7154	Intermediate Similarity	NPC478211
0.7154	Intermediate Similarity	NPC472508
0.7154	Intermediate Similarity	NPC99760
0.7153	Intermediate Similarity	NPC140045
0.7153	Intermediate Similarity	NPC295885
0.7143	Intermediate Similarity	NPC324017
0.7143	Intermediate Similarity	NPC320019
0.7143	Intermediate Similarity	NPC39996
0.7143	Intermediate Similarity	NPC476854
0.7143	Intermediate Similarity	NPC329869

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 NPC476815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	1444
0.2-0.3	3589
0.3-0.4	2592
0.4-0.5	915
0.5-0.6	298
0.6-0.7	117
0.7-0.8	4
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
0.7132	Intermediate Similarity	NPD8513	Phase 3
0.7043	Intermediate Similarity	NPD5779	Approved
0.7043	Intermediate Similarity	NPD5778	Approved
0.704	Intermediate Similarity	NPD6053	Discontinued
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.6983	Remote Similarity	NPD5282	Discontinued
0.694	Remote Similarity	NPD6033	Approved
0.6923	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6335	Approved
0.6899	Remote Similarity	NPD6314	Approved
0.6899	Remote Similarity	NPD6313	Approved
0.6846	Remote Similarity	NPD7100	Approved
0.6846	Remote Similarity	NPD7101	Approved
0.6842	Remote Similarity	NPD7492	Approved
0.6822	Remote Similarity	NPD6009	Approved
0.6794	Remote Similarity	NPD6054	Approved
0.6791	Remote Similarity	NPD6616	Approved
0.6774	Remote Similarity	NPD5697	Approved
0.6772	Remote Similarity	NPD6882	Approved
0.6742	Remote Similarity	NPD5983	Phase 2
0.6742	Remote Similarity	NPD6016	Approved
0.6742	Remote Similarity	NPD6015	Approved
0.6741	Remote Similarity	NPD8074	Phase 3
0.6741	Remote Similarity	NPD7078	Approved
0.672	Remote Similarity	NPD6899	Approved
0.672	Remote Similarity	NPD6881	Approved
0.6694	Remote Similarity	NPD6675	Approved
0.6694	Remote Similarity	NPD7128	Approved
0.6694	Remote Similarity	NPD6402	Approved
0.6694	Remote Similarity	NPD5739	Approved
0.6693	Remote Similarity	NPD6649	Approved
0.6693	Remote Similarity	NPD6650	Approved
0.6693	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6370	Approved
0.6692	Remote Similarity	NPD7115	Discovery
0.6692	Remote Similarity	NPD5988	Approved
0.6691	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6373	Approved
0.664	Remote Similarity	NPD5701	Approved
0.664	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6101	Approved
0.6618	Remote Similarity	NPD8293	Discontinued
0.6615	Remote Similarity	NPD6868	Approved
0.6614	Remote Similarity	NPD6883	Approved
0.6614	Remote Similarity	NPD7290	Approved
0.6614	Remote Similarity	NPD7102	Approved
0.6612	Remote Similarity	NPD5696	Approved
0.6594	Remote Similarity	NPD5956	Approved
0.6589	Remote Similarity	NPD4632	Approved
0.6587	Remote Similarity	NPD7320	Approved
0.6587	Remote Similarity	NPD6011	Approved
0.6583	Remote Similarity	NPD7839	Suspended
0.6562	Remote Similarity	NPD6617	Approved
0.6562	Remote Similarity	NPD6847	Approved
0.6562	Remote Similarity	NPD8130	Phase 1
0.6562	Remote Similarity	NPD6869	Approved
0.6525	Remote Similarity	NPD7983	Approved
0.6525	Remote Similarity	NPD6411	Approved
0.6519	Remote Similarity	NPD8328	Phase 3
0.6512	Remote Similarity	NPD8297	Approved
0.6484	Remote Similarity	NPD5169	Approved
0.6475	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD4225	Approved
0.6457	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5128	Approved
0.6434	Remote Similarity	NPD5216	Approved
0.6434	Remote Similarity	NPD5215	Approved
0.6434	Remote Similarity	NPD5217	Approved
0.6434	Remote Similarity	NPD5127	Approved
0.6393	Remote Similarity	NPD6083	Phase 2
0.6393	Remote Similarity	NPD6084	Phase 2
0.6383	Remote Similarity	NPD6845	Suspended
0.6378	Remote Similarity	NPD6614	Approved
0.6364	Remote Similarity	NPD5654	Approved
0.6364	Remote Similarity	NPD5695	Phase 3
0.6357	Remote Similarity	NPD6371	Approved
0.6357	Remote Similarity	NPD4634	Approved
0.6328	Remote Similarity	NPD6686	Approved
0.632	Remote Similarity	NPD5211	Phase 2
0.6308	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD46	Approved
0.6303	Remote Similarity	NPD6698	Approved
0.6303	Remote Similarity	NPD5785	Approved
0.6299	Remote Similarity	NPD6008	Approved
0.6293	Remote Similarity	NPD1694	Approved
0.629	Remote Similarity	NPD5286	Approved
0.629	Remote Similarity	NPD5285	Approved
0.629	Remote Similarity	NPD4696	Approved
0.6288	Remote Similarity	NPD5167	Approved
0.6286	Remote Similarity	NPD7319	Approved
0.626	Remote Similarity	NPD4755	Approved
0.626	Remote Similarity	NPD5959	Approved
0.625	Remote Similarity	NPD7503	Approved
0.6241	Remote Similarity	NPD6274	Approved
0.6239	Remote Similarity	NPD5786	Approved
0.623	Remote Similarity	NPD5210	Approved
0.623	Remote Similarity	NPD4629	Approved
0.6222	Remote Similarity	NPD4522	Approved
0.622	Remote Similarity	NPD5141	Approved
0.621	Remote Similarity	NPD7638	Approved
0.6202	Remote Similarity	NPD5168	Approved
0.6198	Remote Similarity	NPD6399	Phase 3
0.6194	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD6317	Approved
0.619	Remote Similarity	NPD5224	Approved
0.619	Remote Similarity	NPD5225	Approved
0.619	Remote Similarity	NPD4633	Approved
0.619	Remote Similarity	NPD5226	Approved
0.619	Remote Similarity	NPD5091	Approved
0.6187	Remote Similarity	NPD7507	Approved
0.6167	Remote Similarity	NPD7838	Discovery
0.6161	Remote Similarity	NPD4756	Discovery
0.616	Remote Similarity	NPD4700	Approved
0.616	Remote Similarity	NPD7639	Approved
0.616	Remote Similarity	NPD7640	Approved
0.6159	Remote Similarity	NPD7604	Phase 2
0.6154	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5363	Approved
0.6142	Remote Similarity	NPD5175	Approved
0.6142	Remote Similarity	NPD5174	Approved
0.6131	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD8444	Approved
0.6121	Remote Similarity	NPD7154	Phase 3
0.6116	Remote Similarity	NPD5694	Approved
0.6116	Remote Similarity	NPD5281	Approved
0.6116	Remote Similarity	NPD7637	Suspended
0.6116	Remote Similarity	NPD5284	Approved
0.6116	Remote Similarity	NPD5693	Phase 1
0.6111	Remote Similarity	NPD5223	Approved
0.6107	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD4249	Approved
0.6087	Remote Similarity	NPD8080	Discontinued
0.6087	Remote Similarity	NPD5369	Approved
0.6071	Remote Similarity	NPD8451	Approved
0.605	Remote Similarity	NPD4251	Approved
0.605	Remote Similarity	NPD4250	Approved
0.6048	Remote Similarity	NPD5221	Approved
0.6048	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD4697	Phase 3
0.6048	Remote Similarity	NPD5222	Approved
0.6043	Remote Similarity	NPD7830	Approved
0.6043	Remote Similarity	NPD7829	Approved
0.6034	Remote Similarity	NPD4270	Approved
0.6034	Remote Similarity	NPD4269	Approved
0.6034	Remote Similarity	NPD6435	Approved
0.6033	Remote Similarity	NPD5692	Phase 3
0.6028	Remote Similarity	NPD8448	Approved
0.6017	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD6909	Approved
0.6014	Remote Similarity	NPD6908	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD6672	Approved
0.5984	Remote Similarity	NPD6050	Approved
0.5983	Remote Similarity	NPD6110	Phase 1
0.5966	Remote Similarity	NPD5279	Phase 3
0.5954	Remote Similarity	NPD4730	Approved
0.5954	Remote Similarity	NPD4729	Approved
0.595	Remote Similarity	NPD4753	Phase 2
0.595	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.595	Remote Similarity	NPD1695	Approved
0.594	Remote Similarity	NPD1719	Phase 1
0.5935	Remote Similarity	NPD5133	Approved
0.5933	Remote Similarity	NPD8384	Approved
0.5932	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7642	Approved
0.5923	Remote Similarity	NPD4768	Approved
0.5923	Remote Similarity	NPD4767	Approved
0.5906	Remote Similarity	NPD6648	Approved
0.5903	Remote Similarity	NPD8391	Approved
0.5903	Remote Similarity	NPD8390	Approved
0.5903	Remote Similarity	NPD8392	Approved
0.5902	Remote Similarity	NPD5207	Approved
0.5899	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD6921	Approved
0.5897	Remote Similarity	NPD5209	Approved
0.5897	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD4754	Approved
0.5887	Remote Similarity	NPD7748	Approved
0.5887	Remote Similarity	NPD8342	Approved
0.5887	Remote Similarity	NPD8340	Approved
0.5887	Remote Similarity	NPD8341	Approved
0.5887	Remote Similarity	NPD8299	Approved
0.5882	Remote Similarity	NPD1696	Phase 3
0.5878	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD7236	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