NPASS Compound

Structure

CID322660 OpenBabel06191716162D 47 49 0 0 1 0 0 0 0 0999 V2000 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 1.7321 4.0000 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 4.5000 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 1.7321 3.0000 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 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 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 1.0000 0.0000 C 0 0 2 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 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 0.0000 0.0000 0.0000 C 0 0 2 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 -2.2321 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -4.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 44 1 0 0 0 0 3 7 2 0 0 0 0 3 16 1 0 0 0 0 4 8 2 0 0 0 0 4 17 1 0 0 0 0 5 9 2 0 0 0 0 5 16 1 0 0 0 0 6 10 2 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 11 16 2 0 0 0 0 11 20 1 0 0 0 0 12 17 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 13 31 1 0 0 0 0 14 23 1 0 0 0 0 14 31 1 0 0 0 0 15 24 1 0 0 0 0 15 30 1 0 0 0 0 18 20 2 0 0 0 0 18 32 1 0 0 0 0 19 21 2 0 0 0 0 19 33 1 0 0 0 0 20 34 1 0 0 0 0 21 35 1 0 0 0 0 22 27 1 0 0 0 0 22 45 1 1 0 0 0 23 27 1 0 0 0 0 23 46 1 6 0 0 0 24 36 2 0 0 0 0 24 37 1 0 0 0 0 25 38 2 0 0 0 0 25 45 1 0 0 0 0 26 39 2 0 0 0 0 26 46 1 0 0 0 0 27 47 1 1 0 0 0 28 30 1 0 0 0 0 28 40 2 0 0 0 0 28 47 1 0 0 0 0 29 31 1 0 0 0 0 29 41 2 0 0 0 0 29 44 1 0 0 0 0 30 42 1 0 0 0 0 31 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	660.17
Volume:	625.432
LogP:	1.955
LogD:	0.767
LogS:	-2.579
# Rotatable Bonds:	15
TPSA:	263.88
# H-Bond Aceptor:	16
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.076
Synthetic Accessibility Score:	4.412
Fsp3:	0.323
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.311
MDCK Permeability:	2.4395463697146624e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.766
Human Intestinal Absorption (HIA):	0.953
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	98.03559875488281%
Volume Distribution (VD):	0.35
Pgp-substrate:	2.069093704223633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.127
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.09
CYP2C19-substrate:	0.039
CYP2C9-inhibitor:	0.659
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.174
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	6.764
Half-life (T1/2):	0.95

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.626
Drug-inuced Liver Injury (DILI):	0.858
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.589
Skin Sensitization:	0.136
Carcinogencity:	0.201
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC322660

Natural Product ID:	NPC322660
*Common Name:**	XVRZYODGITYIQZ-CACQTGHNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XVRZYODGITYIQZ-CACQTGHNSA-N
Standard InCHI:	InChI=1S/C31H32O16/c1-30(42,15-24(36)37)28(40)47-27-22(45-25(38)9-5-16-3-7-18(32)20(34)11-16)13-31(43,29(41)44-2)14-23(27)46-26(39)10-6-17-4-8-19(33)21(35)12-17/h3-12,22-23,27,32-35,42-43H,13-15H2,1-2H3,(H,36,37)/b9-5+,10-6+/t22-,23-,27-,30?,31+/m1/s1
SMILES:	COC(=O)[C@]1(O)C[C@@H](OC(=O)/C=C/c2ccc(c(c2)O)O)[C@H]([C@@H](C1)OC(=O)/C=C/c1ccc(c(c1)O)O)OC(=O)C(CC(=O)O)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446012
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*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
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	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	3
Others	1

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	20.1	ug.mL-1	PMID[528348]
NPT1	Others	Radical scavenging activity		IC50	=	4.4	ug.mL-1	PMID[528348]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.3	ug.mL-1	PMID[528348]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	52.0	%	PMID[528348]

☑ 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 NPC322660 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	322
0.1-0.2	1302
0.2-0.3	3148
0.3-0.4	7145
0.4-0.5	10182
0.5-0.6	6161
0.6-0.7	8216
0.7-0.8	5908
0.8-0.85	216
0.85-0.9	44
0.9-0.95	45
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9571	High Similarity	NPC277315
0.9571	High Similarity	NPC472016
0.9571	High Similarity	NPC192831
0.9571	High Similarity	NPC43158
0.9571	High Similarity	NPC258469
0.951	High Similarity	NPC192568
0.951	High Similarity	NPC471076
0.95	High Similarity	NPC297517
0.95	High Similarity	NPC224389
0.95	High Similarity	NPC13818
0.95	High Similarity	NPC471027
0.95	High Similarity	NPC35702
0.95	High Similarity	NPC206095
0.95	High Similarity	NPC477335
0.9433	High Similarity	NPC37331
0.9433	High Similarity	NPC284948
0.9433	High Similarity	NPC220664
0.9433	High Similarity	NPC303090
0.9433	High Similarity	NPC319628
0.9357	High Similarity	NPC476819
0.9357	High Similarity	NPC474875
0.9357	High Similarity	NPC205751
0.9357	High Similarity	NPC476820
0.9357	High Similarity	NPC303683
0.9357	High Similarity	NPC26241
0.9357	High Similarity	NPC274891
0.9357	High Similarity	NPC295492
0.9301	High Similarity	NPC477333
0.9286	High Similarity	NPC302857
0.9286	High Similarity	NPC152942
0.9286	High Similarity	NPC219428
0.9286	High Similarity	NPC142703
0.9286	High Similarity	NPC37250
0.9286	High Similarity	NPC278068
0.9184	High Similarity	NPC477334
0.9149	High Similarity	NPC24295
0.9149	High Similarity	NPC283560
0.9116	High Similarity	NPC306343
0.9085	High Similarity	NPC156709
0.9085	High Similarity	NPC179505
0.9071	High Similarity	NPC233350
0.9071	High Similarity	NPC182217
0.9071	High Similarity	NPC70680
0.906	High Similarity	NPC19380
0.906	High Similarity	NPC146277
0.9048	High Similarity	NPC42464
0.9041	High Similarity	NPC229264
0.9	High Similarity	NPC68517
0.8993	High Similarity	NPC163883
0.8993	High Similarity	NPC93498
0.898	High Similarity	NPC43123
0.8973	High Similarity	NPC98356
0.8944	High Similarity	NPC279676
0.8944	High Similarity	NPC67349
0.8926	High Similarity	NPC252979
0.8882	High Similarity	NPC470896
0.8882	High Similarity	NPC473275
0.8865	High Similarity	NPC106406
0.8816	High Similarity	NPC145425
0.8794	High Similarity	NPC168799
0.8794	High Similarity	NPC155209
0.8784	High Similarity	NPC299090
0.8784	High Similarity	NPC283081
0.8784	High Similarity	NPC143892
0.8784	High Similarity	NPC221383
0.8742	High Similarity	NPC106818
0.8742	High Similarity	NPC95498
0.8742	High Similarity	NPC246566
0.8733	High Similarity	NPC32197
0.8732	High Similarity	NPC474895
0.8723	High Similarity	NPC5419
0.8723	High Similarity	NPC25581
0.8723	High Similarity	NPC18074
0.8723	High Similarity	NPC61
0.8714	High Similarity	NPC237506
0.8714	High Similarity	NPC329344
0.8714	High Similarity	NPC32626
0.8714	High Similarity	NPC217052
0.8707	High Similarity	NPC474692
0.8707	High Similarity	NPC50221
0.8707	High Similarity	NPC114242
0.8684	High Similarity	NPC87403
0.8652	High Similarity	NPC198388
0.8649	High Similarity	NPC53884
0.8649	High Similarity	NPC258671
0.8636	High Similarity	NPC134925
0.8616	High Similarity	NPC128403
0.86	High Similarity	NPC142528
0.8581	High Similarity	NPC121573
0.8581	High Similarity	NPC226738
0.8581	High Similarity	NPC183824
0.8581	High Similarity	NPC22176
0.8581	High Similarity	NPC190587
0.8581	High Similarity	NPC304956
0.8553	High Similarity	NPC300329
0.8544	High Similarity	NPC227297
0.8521	High Similarity	NPC108553
0.8514	High Similarity	NPC285550
0.8506	High Similarity	NPC477299
0.8503	High Similarity	NPC477279
0.8503	High Similarity	NPC38473
0.8487	Intermediate Similarity	NPC259576
0.8487	Intermediate Similarity	NPC221091
0.8471	Intermediate Similarity	NPC44507
0.8456	Intermediate Similarity	NPC470130
0.8446	Intermediate Similarity	NPC477277
0.8446	Intermediate Similarity	NPC477278
0.8442	Intermediate Similarity	NPC44730
0.8438	Intermediate Similarity	NPC471823
0.8435	Intermediate Similarity	NPC289690
0.8435	Intermediate Similarity	NPC288452
0.8429	Intermediate Similarity	NPC475695
0.8408	Intermediate Similarity	NPC469654
0.8392	Intermediate Similarity	NPC318799
0.8357	Intermediate Similarity	NPC132921
0.8355	Intermediate Similarity	NPC120621
0.8355	Intermediate Similarity	NPC248257
0.8355	Intermediate Similarity	NPC473138
0.8355	Intermediate Similarity	NPC28776
0.8355	Intermediate Similarity	NPC1580
0.8355	Intermediate Similarity	NPC472969
0.8344	Intermediate Similarity	NPC40920
0.8344	Intermediate Similarity	NPC223335
0.8333	Intermediate Similarity	NPC160378
0.8333	Intermediate Similarity	NPC203757
0.8323	Intermediate Similarity	NPC475162
0.8323	Intermediate Similarity	NPC327225
0.8323	Intermediate Similarity	NPC475216
0.8323	Intermediate Similarity	NPC16024
0.8323	Intermediate Similarity	NPC475595
0.8323	Intermediate Similarity	NPC83663
0.8323	Intermediate Similarity	NPC61152
0.8323	Intermediate Similarity	NPC44260
0.8323	Intermediate Similarity	NPC266084
0.8323	Intermediate Similarity	NPC205037
0.8323	Intermediate Similarity	NPC473544
0.8323	Intermediate Similarity	NPC475145
0.8323	Intermediate Similarity	NPC3746
0.8313	Intermediate Similarity	NPC223006
0.8313	Intermediate Similarity	NPC272750
0.8313	Intermediate Similarity	NPC173729
0.8313	Intermediate Similarity	NPC134047
0.8312	Intermediate Similarity	NPC140151
0.8312	Intermediate Similarity	NPC243891
0.8311	Intermediate Similarity	NPC105525
0.8311	Intermediate Similarity	NPC12218
0.8311	Intermediate Similarity	NPC225036
0.8311	Intermediate Similarity	NPC75763
0.8301	Intermediate Similarity	NPC75945
0.8301	Intermediate Similarity	NPC476394
0.8301	Intermediate Similarity	NPC92117
0.8301	Intermediate Similarity	NPC98809
0.8298	Intermediate Similarity	NPC168653
0.8298	Intermediate Similarity	NPC118584
0.8298	Intermediate Similarity	NPC251407
0.8288	Intermediate Similarity	NPC18646
0.8278	Intermediate Similarity	NPC228940
0.8276	Intermediate Similarity	NPC471749
0.8269	Intermediate Similarity	NPC469888
0.8258	Intermediate Similarity	NPC476434
0.8258	Intermediate Similarity	NPC75695
0.8258	Intermediate Similarity	NPC267091
0.8255	Intermediate Similarity	NPC9218
0.8252	Intermediate Similarity	NPC226855
0.8252	Intermediate Similarity	NPC94810
0.825	Intermediate Similarity	NPC144557
0.8247	Intermediate Similarity	NPC44378
0.8247	Intermediate Similarity	NPC280753
0.8243	Intermediate Similarity	NPC239943
0.8243	Intermediate Similarity	NPC220942
0.8232	Intermediate Similarity	NPC476370
0.8231	Intermediate Similarity	NPC156892
0.8228	Intermediate Similarity	NPC226759
0.8227	Intermediate Similarity	NPC67951
0.8224	Intermediate Similarity	NPC473867
0.8219	Intermediate Similarity	NPC248150
0.8188	Intermediate Similarity	NPC475530
0.8188	Intermediate Similarity	NPC473799
0.8187	Intermediate Similarity	NPC471869
0.8187	Intermediate Similarity	NPC112418
0.8182	Intermediate Similarity	NPC476374
0.8182	Intermediate Similarity	NPC478242
0.8176	Intermediate Similarity	NPC308976
0.8176	Intermediate Similarity	NPC318826
0.8176	Intermediate Similarity	NPC104222
0.8176	Intermediate Similarity	NPC210501
0.8176	Intermediate Similarity	NPC302583
0.8176	Intermediate Similarity	NPC84789
0.8176	Intermediate Similarity	NPC114791
0.8176	Intermediate Similarity	NPC310252
0.8176	Intermediate Similarity	NPC141331
0.8176	Intermediate Similarity	NPC100558
0.8176	Intermediate Similarity	NPC471750
0.8171	Intermediate Similarity	NPC475058
0.8169	Intermediate Similarity	NPC147192
0.8165	Intermediate Similarity	NPC247629
0.8165	Intermediate Similarity	NPC239019
0.8163	Intermediate Similarity	NPC311742
0.8156	Intermediate Similarity	NPC85565
0.8153	Intermediate Similarity	NPC125487

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 NPC322660 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	787
0.2-0.3	1719
0.3-0.4	2763
0.4-0.5	2017
0.5-0.6	1088
0.6-0.7	416
0.7-0.8	85
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9433	High Similarity	NPD6190	Approved
0.8151	Intermediate Similarity	NPD230	Phase 1
0.8121	Intermediate Similarity	NPD7266	Discontinued
0.805	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3817	Phase 2
0.7826	Intermediate Similarity	NPD3882	Suspended
0.7818	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6166	Phase 2
0.7818	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2801	Approved
0.7811	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7075	Discontinued
0.7751	Intermediate Similarity	NPD7251	Discontinued
0.775	Intermediate Similarity	NPD1934	Approved
0.7702	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6232	Discontinued
0.7692	Intermediate Similarity	NPD6797	Phase 2
0.7665	Intermediate Similarity	NPD7473	Discontinued
0.7647	Intermediate Similarity	NPD7685	Pre-registration
0.7633	Intermediate Similarity	NPD7472	Approved
0.7619	Intermediate Similarity	NPD3818	Discontinued
0.7613	Intermediate Similarity	NPD8166	Discontinued
0.7602	Intermediate Similarity	NPD7808	Phase 3
0.7595	Intermediate Similarity	NPD1512	Approved
0.7593	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7054	Approved
0.7557	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5402	Approved
0.7533	Intermediate Similarity	NPD6233	Phase 2
0.7529	Intermediate Similarity	NPD8434	Phase 2
0.7529	Intermediate Similarity	NPD7074	Phase 3
0.7529	Intermediate Similarity	NPD8150	Discontinued
0.7517	Intermediate Similarity	NPD9269	Phase 2
0.7515	Intermediate Similarity	NPD3751	Discontinued
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.7483	Intermediate Similarity	NPD943	Approved
0.7468	Intermediate Similarity	NPD6799	Approved
0.7468	Intermediate Similarity	NPD1511	Approved
0.7443	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6801	Discontinued
0.7413	Intermediate Similarity	NPD9545	Approved
0.7407	Intermediate Similarity	NPD4380	Phase 2
0.7389	Intermediate Similarity	NPD4628	Phase 3
0.7368	Intermediate Similarity	NPD5844	Phase 1
0.7351	Intermediate Similarity	NPD3764	Approved
0.7347	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD37	Approved
0.731	Intermediate Similarity	NPD7228	Approved
0.729	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4965	Approved
0.7289	Intermediate Similarity	NPD4966	Approved
0.7289	Intermediate Similarity	NPD4967	Phase 2
0.7285	Intermediate Similarity	NPD3027	Phase 3
0.7284	Intermediate Similarity	NPD1653	Approved
0.7278	Intermediate Similarity	NPD3787	Discontinued
0.7273	Intermediate Similarity	NPD7819	Suspended
0.7273	Intermediate Similarity	NPD1465	Phase 2
0.7267	Intermediate Similarity	NPD9494	Approved
0.7255	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2935	Discontinued
0.7241	Intermediate Similarity	NPD9268	Approved
0.7239	Intermediate Similarity	NPD3455	Phase 2
0.7237	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6798	Discontinued
0.7235	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5403	Approved
0.7205	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6599	Discontinued
0.7171	Intermediate Similarity	NPD7095	Approved
0.7168	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5494	Approved
0.7152	Intermediate Similarity	NPD7411	Suspended
0.7152	Intermediate Similarity	NPD6385	Approved
0.7152	Intermediate Similarity	NPD6386	Approved
0.7151	Intermediate Similarity	NPD7435	Discontinued
0.7118	Intermediate Similarity	NPD7199	Phase 2
0.7107	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5401	Approved
0.7097	Intermediate Similarity	NPD447	Suspended
0.7097	Intermediate Similarity	NPD6355	Discontinued
0.7088	Intermediate Similarity	NPD6535	Approved
0.7088	Intermediate Similarity	NPD6534	Approved
0.707	Intermediate Similarity	NPD7033	Discontinued
0.707	Intermediate Similarity	NPD1510	Phase 2
0.7065	Intermediate Similarity	NPD7699	Phase 2
0.7065	Intermediate Similarity	NPD7700	Phase 2
0.7044	Intermediate Similarity	NPD1549	Phase 2
0.7044	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1613	Approved
0.703	Intermediate Similarity	NPD3226	Approved
0.7024	Intermediate Similarity	NPD5353	Approved
0.7024	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD8320	Phase 1
0.7021	Intermediate Similarity	NPD8319	Approved
0.7018	Intermediate Similarity	NPD8127	Discontinued
0.6994	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6781	Approved
0.6989	Remote Similarity	NPD6776	Approved
0.6989	Remote Similarity	NPD6782	Approved
0.6989	Remote Similarity	NPD6780	Approved
0.6989	Remote Similarity	NPD6777	Approved
0.6989	Remote Similarity	NPD6779	Approved
0.6989	Remote Similarity	NPD6778	Approved
0.6982	Remote Similarity	NPD7768	Phase 2
0.6981	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4062	Phase 3
0.6966	Remote Similarity	NPD8312	Approved
0.6966	Remote Similarity	NPD8313	Approved
0.6962	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7240	Approved
0.6949	Remote Similarity	NPD6559	Discontinued
0.6936	Remote Similarity	NPD3926	Phase 2
0.6927	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7874	Approved
0.6923	Remote Similarity	NPD1240	Approved
0.6918	Remote Similarity	NPD1551	Phase 2
0.6918	Remote Similarity	NPD9570	Approved
0.6918	Remote Similarity	NPD2796	Approved
0.6901	Remote Similarity	NPD919	Approved
0.6899	Remote Similarity	NPD7097	Phase 1
0.6897	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2533	Approved
0.689	Remote Similarity	NPD2534	Approved
0.689	Remote Similarity	NPD2532	Approved
0.6883	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7697	Approved
0.6878	Remote Similarity	NPD7696	Phase 3
0.6878	Remote Similarity	NPD7698	Approved
0.6871	Remote Similarity	NPD5536	Phase 2
0.6864	Remote Similarity	NPD8455	Phase 2
0.6859	Remote Similarity	NPD6663	Approved
0.6854	Remote Similarity	NPD8368	Discontinued
0.6852	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7871	Phase 2
0.6842	Remote Similarity	NPD7870	Phase 2
0.6842	Remote Similarity	NPD3749	Approved
0.6839	Remote Similarity	NPD5242	Approved
0.6835	Remote Similarity	NPD1607	Approved
0.6823	Remote Similarity	NPD7701	Phase 2
0.6821	Remote Similarity	NPD1608	Approved
0.6821	Remote Similarity	NPD1247	Approved
0.6821	Remote Similarity	NPD6959	Discontinued
0.6818	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5736	Approved
0.6815	Remote Similarity	NPD826	Approved
0.6815	Remote Similarity	NPD825	Approved
0.6815	Remote Similarity	NPD4060	Phase 1
0.6813	Remote Similarity	NPD5408	Approved
0.6813	Remote Similarity	NPD5405	Approved
0.6813	Remote Similarity	NPD5404	Approved
0.6813	Remote Similarity	NPD5406	Approved
0.6803	Remote Similarity	NPD9493	Approved
0.6797	Remote Similarity	NPD1470	Approved
0.6788	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD8151	Discontinued
0.6783	Remote Similarity	NPD3021	Approved
0.6783	Remote Similarity	NPD3022	Approved
0.6776	Remote Similarity	NPD8361	Approved
0.6776	Remote Similarity	NPD8360	Approved
0.6774	Remote Similarity	NPD6832	Phase 2
0.6772	Remote Similarity	NPD4340	Discontinued
0.6772	Remote Similarity	NPD1933	Approved
0.6761	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7039	Approved
0.676	Remote Similarity	NPD7038	Approved
0.6748	Remote Similarity	NPD4110	Phase 3
0.6748	Remote Similarity	NPD3750	Approved
0.6748	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.674	Remote Similarity	NPD8407	Phase 2
0.674	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4357	Discontinued
0.6727	Remote Similarity	NPD7390	Discontinued
0.6726	Remote Similarity	NPD7458	Discontinued
0.6718	Remote Similarity	NPD7801	Approved
0.6707	Remote Similarity	NPD3887	Approved
0.6707	Remote Similarity	NPD2354	Approved
0.6704	Remote Similarity	NPD5953	Discontinued
0.6688	Remote Similarity	NPD1203	Approved
0.6687	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3146	Approved
0.6686	Remote Similarity	NPD7229	Phase 3
0.6685	Remote Similarity	NPD8435	Approved
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7972	Discontinued
0.6667	Remote Similarity	NPD2629	Approved
0.6667	Remote Similarity	NPD555	Phase 2
0.6647	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2799	Discontinued
0.6645	Remote Similarity	NPD1535	Discovery

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