NPASS Compound

Structure

CID214368 OpenBabel06191716002D 31 34 0 0 1 0 0 0 0 0999 V2000 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 C 0 0 0 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 3.5000 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 5.1962 3.0000 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 0.0000 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 0.8660 0.5000 0.0000 C 0 0 1 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 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 7 1 0 0 0 0 2 12 1 0 0 0 0 3 7 2 0 0 0 0 3 9 1 0 0 0 0 4 8 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 5 13 2 0 0 0 0 6 7 1 0 0 0 0 6 25 1 0 0 0 0 8 11 1 0 0 0 0 8 24 1 0 0 0 0 9 12 2 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 23 2 0 0 0 0 11 26 2 0 0 0 0 12 31 1 0 0 0 0 13 31 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 16 24 1 6 0 0 0 17 27 2 0 0 0 0 18 19 1 0 0 0 0 18 28 1 6 0 0 0 19 29 1 1 0 0 0 20 22 2 0 0 0 0 20 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.12
Volume:	399.404
LogP:	2.406
LogD:	0.181
LogS:	-4.996
# Rotatable Bonds:	4
TPSA:	203.55
# H-Bond Aceptor:	11
# H-Bond Donor:	11
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.132
Synthetic Accessibility Score:	3.24
Fsp3:	0.05
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.516
MDCK Permeability:	3.0731828246644e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.856
Human Intestinal Absorption (HIA):	0.069
20% Bioavailability (F20%):	0.938
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	98.91834259033203%
Volume Distribution (VD):	0.448
Pgp-substrate:	5.240379810333252%

ADMET: Metabolism

CYP1A2-inhibitor:	0.367
CYP1A2-substrate:	0.145
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.353
CYP2C9-substrate:	0.313
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.048

ADMET: Excretion

Clearance (CL):	4.833
Half-life (T1/2):	0.686

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.382
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.955
Carcinogencity:	0.273
Eye Corrosion:	0.003
Eye Irritation:	0.074
Respiratory Toxicity:	0.506

Download Data

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

Natural Product: NPC214368

Natural Product ID:	NPC214368
*Common Name:**	Pitucamycin
IUPAC Name:	(3R,4R,5R)-2-amino-3,4-dihydroxy-5-[[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino]-6-oxocyclohexene-1-carboxamide
Synonyms:	Pitucamycin
Standard InCHIKey:	NURWOUVTSOIROK-QXAKKESOSA-N
Standard InCHI:	InChI=1S/C20H18N4O7/c21-15-14(20(22)30)17(27)16(19(29)18(15)28)24-8-4-10-13(5-11(8)26)31-12-2-1-7(6-25)3-9(12)23-10/h1-5,16,18-19,24-25,28-29H,6,21H2,(H2,22,30)/t16-,18+,19+/m0/s1
SMILES:	c1cc2c(cc1CO)nc1-c(cc(=O)c(c1)N[C@H]1C(=O)C(=C([C@H]([C@@H]1O)O)N)C(=N)O)o2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224596
PubChem CID:	46939682
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001396] Benzoxazines [CHEMONTID:0001855] Phenoxazines

*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
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17880174]
NPO1526	Ratibida latipalearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800631]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10867	Graphis elongata	Species	Aclididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11355	Homarus americanus	Species	Nephropidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9020	Eriostemon fitzgeraldii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12481	Croton californicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12309	Malva crispa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8547	Petasites niveus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12535	Solanum toxicarium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7365	Clibadium pentaneuron	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3900	Phellinus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7883	Albugo candida	Species	Albuginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3202	0lina erumpens	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24849	Rhinella paracnemis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9227	Xylaria berteri	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2805	Distolasterias nipon	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1937	Andropogon nardus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO729	Espeletia marcana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5219	Dendrobium rotundatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9320	Weddellina squamulosa	Species	Podostemaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6787	Neoalsomitra integrifolia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18350	Culcitium canescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9937	Piptolepis leptospermoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1526	Ratibida latipalearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	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
GI50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	CC50	=	74800.0	nM	PMID[544345]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	27600.0	nM	PMID[544345]
NPT737	Cell Line	HUVEC	Homo sapiens	GI50	=	36600.0	nM	PMID[544345]

☑ 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 NPC214368 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	466
0.1-0.2	3627
0.2-0.3	12704
0.3-0.4	5317
0.4-0.5	14478
0.5-0.6	5183
0.6-0.7	874
0.7-0.8	39
0.8-0.85	4
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8315	Intermediate Similarity	NPC57105
0.8156	Intermediate Similarity	NPC231862
0.8077	Intermediate Similarity	NPC314861
0.772	Intermediate Similarity	NPC313886
0.7684	Intermediate Similarity	NPC315631
0.7638	Intermediate Similarity	NPC108847
0.7594	Intermediate Similarity	NPC127362
0.7277	Intermediate Similarity	NPC314817
0.7277	Intermediate Similarity	NPC66191
0.7277	Intermediate Similarity	NPC316297
0.7268	Intermediate Similarity	NPC8467
0.7171	Intermediate Similarity	NPC478049
0.7163	Intermediate Similarity	NPC311357
0.7136	Intermediate Similarity	NPC469829
0.7107	Intermediate Similarity	NPC316161
0.7095	Intermediate Similarity	NPC473422
0.7087	Intermediate Similarity	NPC314948
0.6966	Remote Similarity	NPC208022
0.6927	Remote Similarity	NPC297584
0.6915	Remote Similarity	NPC469831
0.6897	Remote Similarity	NPC262725
0.6885	Remote Similarity	NPC314113
0.6863	Remote Similarity	NPC469830
0.6859	Remote Similarity	NPC10875
0.6859	Remote Similarity	NPC10730
0.6835	Remote Similarity	NPC326027
0.682	Remote Similarity	NPC326333
0.6796	Remote Similarity	NPC283207
0.6765	Remote Similarity	NPC477391
0.6739	Remote Similarity	NPC47986
0.6738	Remote Similarity	NPC119569
0.673	Remote Similarity	NPC323662
0.6729	Remote Similarity	NPC473460
0.6714	Remote Similarity	NPC472330
0.6714	Remote Similarity	NPC472329
0.67	Remote Similarity	NPC472163
0.6685	Remote Similarity	NPC307123
0.6685	Remote Similarity	NPC247018
0.6685	Remote Similarity	NPC97870
0.6684	Remote Similarity	NPC473804
0.6683	Remote Similarity	NPC83241
0.6682	Remote Similarity	NPC470746
0.6682	Remote Similarity	NPC471336
0.6667	Remote Similarity	NPC471532
0.6651	Remote Similarity	NPC477160
0.665	Remote Similarity	NPC204179
0.6634	Remote Similarity	NPC477392
0.6634	Remote Similarity	NPC315934
0.6633	Remote Similarity	NPC471568
0.6633	Remote Similarity	NPC473693
0.663	Remote Similarity	NPC313466
0.6622	Remote Similarity	NPC471531
0.662	Remote Similarity	NPC87714
0.6619	Remote Similarity	NPC328763
0.6617	Remote Similarity	NPC95412
0.6602	Remote Similarity	NPC315542
0.6602	Remote Similarity	NPC299806
0.6602	Remote Similarity	NPC235194
0.6598	Remote Similarity	NPC56635
0.6591	Remote Similarity	NPC92235
0.6579	Remote Similarity	NPC245974
0.6568	Remote Similarity	NPC469722
0.6567	Remote Similarity	NPC248670
0.656	Remote Similarity	NPC478075
0.6553	Remote Similarity	NPC41501
0.6524	Remote Similarity	NPC189724
0.6524	Remote Similarity	NPC83289
0.6524	Remote Similarity	NPC212850
0.6518	Remote Similarity	NPC321226
0.6518	Remote Similarity	NPC328856
0.6518	Remote Similarity	NPC478047
0.6518	Remote Similarity	NPC478046
0.6518	Remote Similarity	NPC180210
0.6518	Remote Similarity	NPC314914
0.6515	Remote Similarity	NPC158900
0.6514	Remote Similarity	NPC195787
0.6514	Remote Similarity	NPC246140
0.6509	Remote Similarity	NPC475843
0.6497	Remote Similarity	NPC306366
0.6495	Remote Similarity	NPC477550
0.6495	Remote Similarity	NPC477552
0.6489	Remote Similarity	NPC284236
0.6489	Remote Similarity	NPC316368
0.6482	Remote Similarity	NPC254700
0.648	Remote Similarity	NPC70549
0.6476	Remote Similarity	NPC174629
0.6474	Remote Similarity	NPC247298
0.6473	Remote Similarity	NPC478048
0.6471	Remote Similarity	NPC291609
0.6468	Remote Similarity	NPC314702
0.6468	Remote Similarity	NPC196091
0.6465	Remote Similarity	NPC133470
0.6465	Remote Similarity	NPC191863
0.6465	Remote Similarity	NPC289776
0.6463	Remote Similarity	NPC122886
0.6462	Remote Similarity	NPC474678
0.6462	Remote Similarity	NPC471338
0.6457	Remote Similarity	NPC30749
0.6456	Remote Similarity	NPC270301
0.6452	Remote Similarity	NPC474077
0.6445	Remote Similarity	NPC475411
0.6445	Remote Similarity	NPC28510
0.644	Remote Similarity	NPC9373
0.6438	Remote Similarity	NPC472286
0.6438	Remote Similarity	NPC472287
0.6435	Remote Similarity	NPC477551
0.6432	Remote Similarity	NPC470441
0.6432	Remote Similarity	NPC170101
0.6429	Remote Similarity	NPC124300
0.6429	Remote Similarity	NPC112766
0.6425	Remote Similarity	NPC315632
0.6422	Remote Similarity	NPC168153
0.6418	Remote Similarity	NPC186617
0.6413	Remote Similarity	NPC274732
0.6411	Remote Similarity	NPC276120
0.6404	Remote Similarity	NPC99724
0.6404	Remote Similarity	NPC273755
0.6402	Remote Similarity	NPC470023
0.6402	Remote Similarity	NPC316224
0.6402	Remote Similarity	NPC204546
0.6396	Remote Similarity	NPC25961
0.6393	Remote Similarity	NPC14339
0.6389	Remote Similarity	NPC123859
0.6384	Remote Similarity	NPC217903
0.638	Remote Similarity	NPC329567
0.638	Remote Similarity	NPC330683
0.6376	Remote Similarity	NPC148124
0.6372	Remote Similarity	NPC470021
0.6371	Remote Similarity	NPC470784
0.6368	Remote Similarity	NPC473378
0.6368	Remote Similarity	NPC218303
0.6368	Remote Similarity	NPC473407
0.6368	Remote Similarity	NPC146418
0.6364	Remote Similarity	NPC301163
0.6364	Remote Similarity	NPC26928
0.6364	Remote Similarity	NPC477161
0.636	Remote Similarity	NPC313627
0.636	Remote Similarity	NPC274268
0.6359	Remote Similarity	NPC45037
0.6359	Remote Similarity	NPC269750
0.6359	Remote Similarity	NPC194671
0.6359	Remote Similarity	NPC123140
0.6359	Remote Similarity	NPC242728
0.6359	Remote Similarity	NPC475421
0.6359	Remote Similarity	NPC471337
0.6356	Remote Similarity	NPC176113
0.6354	Remote Similarity	NPC320242
0.6354	Remote Similarity	NPC473769
0.6351	Remote Similarity	NPC471561
0.635	Remote Similarity	NPC139506
0.635	Remote Similarity	NPC292143
0.6349	Remote Similarity	NPC469360
0.6349	Remote Similarity	NPC310618
0.6344	Remote Similarity	NPC77777
0.6341	Remote Similarity	NPC50016
0.6339	Remote Similarity	NPC116178
0.6339	Remote Similarity	NPC305542
0.6336	Remote Similarity	NPC248903
0.6335	Remote Similarity	NPC16249
0.6335	Remote Similarity	NPC257266
0.6329	Remote Similarity	NPC184680
0.6327	Remote Similarity	NPC471335
0.6327	Remote Similarity	NPC288349
0.6324	Remote Similarity	NPC73280
0.6324	Remote Similarity	NPC470392
0.6324	Remote Similarity	NPC471953
0.6321	Remote Similarity	NPC132771
0.6321	Remote Similarity	NPC474059
0.632	Remote Similarity	NPC19175
0.6316	Remote Similarity	NPC294951
0.6313	Remote Similarity	NPC317727
0.6311	Remote Similarity	NPC9475
0.6307	Remote Similarity	NPC208522
0.6306	Remote Similarity	NPC257728
0.6305	Remote Similarity	NPC46009
0.6304	Remote Similarity	NPC473987
0.6303	Remote Similarity	NPC301501
0.6303	Remote Similarity	NPC470785
0.6301	Remote Similarity	NPC472435
0.6301	Remote Similarity	NPC288759
0.6296	Remote Similarity	NPC472191
0.6296	Remote Similarity	NPC144314
0.6293	Remote Similarity	NPC473354
0.6293	Remote Similarity	NPC314222
0.6293	Remote Similarity	NPC266994
0.6293	Remote Similarity	NPC471165
0.6293	Remote Similarity	NPC158277
0.6293	Remote Similarity	NPC196449
0.6291	Remote Similarity	NPC70340
0.6289	Remote Similarity	NPC324081
0.6286	Remote Similarity	NPC138083
0.6286	Remote Similarity	NPC133591
0.6278	Remote Similarity	NPC153365
0.6277	Remote Similarity	NPC473055
0.6277	Remote Similarity	NPC473052
0.6272	Remote Similarity	NPC469594
0.6269	Remote Similarity	NPC17760
0.6269	Remote Similarity	NPC472923
0.6268	Remote Similarity	NPC470903
0.6268	Remote Similarity	NPC314659

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 NPC214368 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	688
0.2-0.3	1042
0.3-0.4	1777
0.4-0.5	2890
0.5-0.6	2036
0.6-0.7	464
0.7-0.8	15
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
0.7865	Intermediate Similarity	NPD3154	Approved
0.7865	Intermediate Similarity	NPD3153	Approved
0.7568	Intermediate Similarity	NPD3560	Approved
0.7568	Intermediate Similarity	NPD3557	Approved
0.7568	Intermediate Similarity	NPD3558	Approved
0.7568	Intermediate Similarity	NPD3559	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3556	Approved
0.7426	Intermediate Similarity	NPD4604	Approved
0.7426	Intermediate Similarity	NPD4605	Approved
0.7382	Intermediate Similarity	NPD2215	Approved
0.7382	Intermediate Similarity	NPD2216	Approved
0.73	Intermediate Similarity	NPD4258	Approved
0.73	Intermediate Similarity	NPD4259	Approved
0.7277	Intermediate Similarity	NPD2249	Approved
0.7277	Intermediate Similarity	NPD2247	Approved
0.7241	Intermediate Similarity	NPD7256	Discontinued
0.7184	Intermediate Similarity	NPD5547	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7476	Discontinued
0.7062	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3778	Approved
0.7015	Intermediate Similarity	NPD6045	Phase 3
0.7014	Intermediate Similarity	NPD4465	Phase 2
0.7014	Intermediate Similarity	NPD4467	Phase 2
0.6995	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7043	Discontinued
0.6946	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4083	Discontinued
0.6934	Remote Similarity	NPD7891	Discontinued
0.6923	Remote Similarity	NPD1422	Approved
0.6923	Remote Similarity	NPD6034	Phase 2
0.6912	Remote Similarity	NPD1898	Discontinued
0.6884	Remote Similarity	NPD3965	Phase 1
0.6881	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6283	Phase 2
0.6872	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6104	Discontinued
0.6861	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1012	Discontinued
0.6829	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD2843	Phase 2
0.6796	Remote Similarity	NPD2845	Phase 2
0.6784	Remote Similarity	NPD6199	Discontinued
0.6783	Remote Similarity	NPD7853	Phase 2
0.6777	Remote Similarity	NPD7810	Phase 3
0.6777	Remote Similarity	NPD7811	Phase 3
0.6776	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2514	Approved
0.6751	Remote Similarity	NPD2680	Approved
0.6751	Remote Similarity	NPD2681	Approved
0.6745	Remote Similarity	NPD6519	Phase 2
0.6745	Remote Similarity	NPD2339	Phase 3
0.6743	Remote Similarity	NPD4502	Phase 2
0.67	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.67	Remote Similarity	NPD2525	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1423	Approved
0.6683	Remote Similarity	NPD5641	Discontinued
0.6682	Remote Similarity	NPD5845	Phase 2
0.6682	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD3945	Discontinued
0.6667	Remote Similarity	NPD3180	Approved
0.6667	Remote Similarity	NPD7318	Phase 3
0.6667	Remote Similarity	NPD3179	Approved
0.6667	Remote Similarity	NPD7883	Discontinued
0.6667	Remote Similarity	NPD3052	Approved
0.6667	Remote Similarity	NPD3054	Approved
0.6635	Remote Similarity	NPD6136	Phase 2
0.6635	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3536	Discontinued
0.6631	Remote Similarity	NPD2459	Approved
0.6631	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD2458	Approved
0.6631	Remote Similarity	NPD2460	Phase 3
0.6622	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6874	Approved
0.6619	Remote Similarity	NPD5150	Phase 2
0.6597	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6719	Approved
0.6591	Remote Similarity	NPD1945	Phase 1
0.6591	Remote Similarity	NPD5416	Discontinued
0.6587	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD8461	Discontinued
0.6583	Remote Similarity	NPD7484	Phase 3
0.6583	Remote Similarity	NPD7485	Phase 3
0.6579	Remote Similarity	NPD3263	Phase 3
0.6574	Remote Similarity	NPD3802	Phase 3
0.6567	Remote Similarity	NPD2248	Approved
0.6567	Remote Similarity	NPD2246	Approved
0.6565	Remote Similarity	NPD5022	Discontinued
0.6564	Remote Similarity	NPD7317	Phase 3
0.6564	Remote Similarity	NPD1769	Discontinued
0.6559	Remote Similarity	NPD2239	Approved
0.6559	Remote Similarity	NPD2240	Approved
0.6553	Remote Similarity	NPD7546	Discontinued
0.6549	Remote Similarity	NPD7556	Discontinued
0.6538	Remote Similarity	NPD4587	Phase 3
0.6538	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.653	Remote Similarity	NPD4082	Approved
0.6528	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6863	Phase 2
0.6528	Remote Similarity	NPD6510	Phase 1
0.6528	Remote Similarity	NPD5267	Discontinued
0.6528	Remote Similarity	NPD6511	Phase 1
0.6528	Remote Similarity	NPD7316	Discontinued
0.6528	Remote Similarity	NPD4003	Phase 3
0.6526	Remote Similarity	NPD5872	Discontinued
0.6518	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4255	Phase 1
0.651	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD3490	Discontinued
0.6507	Remote Similarity	NPD5640	Discontinued
0.6504	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD6289	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6063	Approved
0.6493	Remote Similarity	NPD4740	Approved
0.649	Remote Similarity	NPD6339	Approved
0.649	Remote Similarity	NPD6340	Approved
0.6489	Remote Similarity	NPD6198	Phase 1
0.6488	Remote Similarity	NPD5553	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD3823	Discontinued
0.6488	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2434	Approved
0.6479	Remote Similarity	NPD3659	Discontinued
0.6478	Remote Similarity	NPD7994	Phase 2
0.6477	Remote Similarity	NPD7131	Phase 3
0.6474	Remote Similarity	NPD5160	Discontinued
0.6471	Remote Similarity	NPD5645	Phase 3
0.6471	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7608	Discontinued
0.6465	Remote Similarity	NPD7565	Approved
0.6462	Remote Similarity	NPD4466	Phase 1
0.6459	Remote Similarity	NPD4515	Suspended
0.6458	Remote Similarity	NPD4661	Approved
0.6458	Remote Similarity	NPD4662	Approved
0.6458	Remote Similarity	NPD3985	Discontinued
0.6458	Remote Similarity	NPD2874	Phase 2
0.6453	Remote Similarity	NPD5938	Phase 3
0.6452	Remote Similarity	NPD8162	Phase 2
0.6452	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.645	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD8311	Discontinued
0.6445	Remote Similarity	NPD5871	Discontinued
0.6442	Remote Similarity	NPD4586	Phase 3
0.6438	Remote Similarity	NPD6807	Phase 3
0.6438	Remote Similarity	NPD7031	Phase 1
0.6436	Remote Similarity	NPD2388	Discontinued
0.6435	Remote Similarity	NPD7186	Phase 3
0.6429	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4157	Discontinued
0.6429	Remote Similarity	NPD6716	Phase 1
0.6422	Remote Similarity	NPD3909	Discontinued
0.6422	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD2821	Approved
0.6411	Remote Similarity	NPD6967	Phase 2
0.6409	Remote Similarity	NPD7584	Approved
0.6409	Remote Similarity	NPD7263	Phase 2
0.6404	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3952	Approved
0.6404	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3951	Phase 3
0.6402	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8149	Discontinued
0.6398	Remote Similarity	NPD7628	Phase 3
0.6398	Remote Similarity	NPD7630	Phase 3
0.6398	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6644	Discontinued
0.6392	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD4505	Phase 1
0.6388	Remote Similarity	NPD6974	Phase 3
0.638	Remote Similarity	NPD4022	Approved
0.638	Remote Similarity	NPD7300	Phase 3
0.638	Remote Similarity	NPD3472	Approved
0.638	Remote Similarity	NPD2907	Approved
0.638	Remote Similarity	NPD7302	Phase 3
0.638	Remote Similarity	NPD2906	Approved
0.6377	Remote Similarity	NPD7039	Approved
0.6377	Remote Similarity	NPD7038	Approved
0.6376	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD7626	Approved
0.6376	Remote Similarity	NPD7627	Approved
0.6374	Remote Similarity	NPD4993	Discontinued
0.6373	Remote Similarity	NPD4123	Phase 3
0.6373	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5650	Approved
0.6372	Remote Similarity	NPD5651	Approved
0.6372	Remote Similarity	NPD5652	Approved
0.6364	Remote Similarity	NPD6905	Phase 2
0.636	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5557	Phase 1
0.6356	Remote Similarity	NPD4679	Discontinued
0.6354	Remote Similarity	NPD1817	Approved
0.6354	Remote Similarity	NPD1819	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