NPASS Compound

Structure

NPC126984 OpenBabel07101718332D 50 56 0 0 1 0 0 0 0 0999 V2000 2.5305 -4.5384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5604 -2.5386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7453 -1.2364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8123 -0.0327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4053 -2.0565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9123 1.0095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4204 0.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6720 -4.0255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4354 4.3614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4755 4.0809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1582 3.6703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2385 3.1094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9211 2.6988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3143 0.6301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1234 0.0424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2453 1.3024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9927 1.5038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1553 -0.3215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8143 -0.9087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1069 -2.5514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 -3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7453 -0.2364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8721 -1.0309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9613 2.4184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5053 0.0424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5543 0.3514 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2453 1.3024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1431 -1.1345 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5272 0.1950 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3016 2.2266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9362 0.3514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8884 -1.4869 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8285 -2.5127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7242 1.4469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4999 -1.6319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7665 -1.4782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6530 3.1629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 -2.9997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4470 0.7558 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8143 -0.9087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1109 -2.4618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0375 -1.5818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6944 2.1370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7643 1.1665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 -1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 8 21 2 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 24 2 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 25 1 0 0 0 0 15 45 1 0 0 0 0 16 26 1 0 0 0 0 17 28 1 0 0 0 0 17 31 1 0 0 0 0 18 29 1 0 0 0 0 18 30 1 0 0 0 0 19 25 2 0 0 0 0 19 45 1 0 0 0 0 20 38 1 0 0 0 0 20 46 1 0 0 0 0 21 36 1 0 0 0 0 22 26 1 0 0 0 0 22 32 2 0 0 0 0 23 41 2 0 0 0 0 23 47 1 0 0 0 0 24 37 1 0 0 0 0 26 25 1 1 0 0 0 27 16 1 1 0 0 0 27 32 1 0 0 0 0 27 48 1 0 0 0 0 28 39 1 1 0 0 0 28 40 1 0 0 0 0 29 38 1 6 0 0 0 29 47 1 0 0 0 0 30 39 1 6 0 0 0 30 49 1 0 0 0 0 31 42 2 0 0 0 0 31 48 1 0 0 0 0 32 40 1 0 0 0 0 33 34 1 0 0 0 0 33 35 1 0 0 0 0 33 46 1 6 0 0 0 34 38 1 1 0 0 0 34 39 1 0 0 0 0 35 40 1 6 0 0 0 35 50 1 0 0 0 0 36 43 2 0 0 0 0 36 50 1 0 0 0 0 37 44 2 0 0 0 0 37 49 1 0 0 0 0 38 5 1 1 0 0 0 39 6 1 1 0 0 0 40 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	686.31
Volume:	699.402
LogP:	4.863
LogD:	3.961
LogS:	-5.191
# Rotatable Bonds:	9
TPSA:	127.57
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.144
Synthetic Accessibility Score:	5.585
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.109
MDCK Permeability:	3.600391573854722e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.923
30% Bioavailability (F30%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	98.51991271972656%
Volume Distribution (VD):	3.193
Pgp-substrate:	7.141388416290283%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.057
CYP2C19-inhibitor:	0.771
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.894
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.28
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.89
CYP3A4-substrate:	0.617

ADMET: Excretion

Clearance (CL):	8.758
Half-life (T1/2):	0.453

ADMET: Toxicity

hERG Blockers:	0.307
Human Hepatotoxicity (H-HT):	0.969
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.756
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.05
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.056
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC126984

Natural Product ID:	NPC126984
*Common Name:**	1-O-Deacetyl-1-O-Benzoylohchinolide B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XAZZMXXFVRTLFW-MSEKIEPGSA-N
Standard InCHI:	InChI=1S/C40H46O10/c1-8-21(2)36(43)50-35-33-34-38(5,20-46-33)29(47-23(4)41)18-30(49-37(44)24-12-10-9-11-13-24)39(34,6)28-17-31(42)48-27-16-26(25-14-15-45-19-25)22(3)32(27)40(28,35)7/h8-15,19,26-30,33-35H,16-18,20H2,1-7H3/b21-8+/t26-,27+,28-,29-,30+,33-,34+,35-,38-,39+,40-/m1/s1
SMILES:	C/C=C(/C(=O)O[C@@H]1[C@@H]2OC[C@]3([C@H]2[C@]([C@@H]2[C@]1(C)C1=C(C)[C@@H](C[C@@H]1OC(=O)C2)c1ccoc1)(C)[C@@H](OC(=O)c1ccccc1)C[C@H]3OC(=O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506953
PubChem CID:	11433925
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932	Melia azedarach	Species	Meliaceae	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	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	Activity	=	100.0	%	PMID[489940]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	33000.0	nM	PMID[489940]

☑ 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 NPC126984 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	428
0.1-0.2	1488
0.2-0.3	2807
0.3-0.4	6130
0.4-0.5	11321
0.5-0.6	7668
0.6-0.7	9992
0.7-0.8	2522
0.8-0.85	256
0.85-0.9	70
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC62692
1.0	High Similarity	NPC27541
0.9745	High Similarity	NPC118086
0.9742	High Similarity	NPC61967
0.9437	High Similarity	NPC475641
0.9437	High Similarity	NPC475237
0.9412	High Similarity	NPC182427
0.9412	High Similarity	NPC29695
0.9387	High Similarity	NPC11062
0.9241	High Similarity	NPC471003
0.9172	High Similarity	NPC475066
0.9161	High Similarity	NPC322546
0.9161	High Similarity	NPC308205
0.913	High Similarity	NPC310572
0.9062	High Similarity	NPC14499
0.9062	High Similarity	NPC475039
0.9062	High Similarity	NPC476035
0.9018	High Similarity	NPC88593
0.8994	High Similarity	NPC472671
0.8961	High Similarity	NPC71821
0.8931	High Similarity	NPC214495
0.8931	High Similarity	NPC195954
0.8931	High Similarity	NPC88007
0.8931	High Similarity	NPC469847
0.8931	High Similarity	NPC470119
0.8889	High Similarity	NPC276735
0.8882	High Similarity	NPC470792
0.8875	High Similarity	NPC475226
0.8834	High Similarity	NPC472670
0.8834	High Similarity	NPC307781
0.8827	High Similarity	NPC285567
0.882	High Similarity	NPC8389
0.8812	High Similarity	NPC194499
0.8797	High Similarity	NPC472672
0.8765	High Similarity	NPC79571
0.8765	High Similarity	NPC68848
0.8742	High Similarity	NPC34421
0.8742	High Similarity	NPC253201
0.8742	High Similarity	NPC237259
0.8742	High Similarity	NPC302054
0.8742	High Similarity	NPC98206
0.8735	High Similarity	NPC294512
0.8734	High Similarity	NPC116717
0.8726	High Similarity	NPC470790
0.8726	High Similarity	NPC471001
0.8726	High Similarity	NPC470791
0.872	High Similarity	NPC277618
0.8712	High Similarity	NPC283209
0.8696	High Similarity	NPC7059
0.8679	High Similarity	NPC121615
0.8679	High Similarity	NPC294511
0.8671	High Similarity	NPC212257
0.865	High Similarity	NPC188649
0.8634	High Similarity	NPC104736
0.8634	High Similarity	NPC41880
0.8614	High Similarity	NPC296558
0.8614	High Similarity	NPC472673
0.8598	High Similarity	NPC88841
0.8598	High Similarity	NPC472669
0.8598	High Similarity	NPC288602
0.858	High Similarity	NPC304692
0.858	High Similarity	NPC246841
0.858	High Similarity	NPC56953
0.858	High Similarity	NPC470118
0.858	High Similarity	NPC167142
0.858	High Similarity	NPC1408
0.858	High Similarity	NPC176413
0.8571	High Similarity	NPC25351
0.8553	High Similarity	NPC156189
0.8553	High Similarity	NPC228842
0.8535	High Similarity	NPC470999
0.8503	High Similarity	NPC291742
0.85	High Similarity	NPC291150
0.85	High Similarity	NPC18135
0.8494	Intermediate Similarity	NPC86800
0.8494	Intermediate Similarity	NPC121995
0.8485	Intermediate Similarity	NPC471168
0.8485	Intermediate Similarity	NPC469846
0.8481	Intermediate Similarity	NPC255414
0.8476	Intermediate Similarity	NPC470789
0.8466	Intermediate Similarity	NPC197137
0.8462	Intermediate Similarity	NPC469848
0.8457	Intermediate Similarity	NPC476262
0.8457	Intermediate Similarity	NPC141538
0.8457	Intermediate Similarity	NPC155939
0.8457	Intermediate Similarity	NPC296807
0.8452	Intermediate Similarity	NPC302392
0.8447	Intermediate Similarity	NPC471002
0.8447	Intermediate Similarity	NPC476201
0.8443	Intermediate Similarity	NPC270312
0.8438	Intermediate Similarity	NPC5180
0.8434	Intermediate Similarity	NPC159520
0.8428	Intermediate Similarity	NPC471007
0.8424	Intermediate Similarity	NPC471167
0.8424	Intermediate Similarity	NPC472668
0.8424	Intermediate Similarity	NPC471166
0.8424	Intermediate Similarity	NPC18986
0.8415	Intermediate Similarity	NPC84349
0.8415	Intermediate Similarity	NPC474611
0.8385	Intermediate Similarity	NPC471000
0.8383	Intermediate Similarity	NPC308156
0.8383	Intermediate Similarity	NPC472141
0.8375	Intermediate Similarity	NPC69647
0.8375	Intermediate Similarity	NPC125182
0.8365	Intermediate Similarity	NPC216755
0.8364	Intermediate Similarity	NPC287559
0.8363	Intermediate Similarity	NPC167340
0.8354	Intermediate Similarity	NPC472778
0.8354	Intermediate Similarity	NPC472777
0.8354	Intermediate Similarity	NPC472776
0.8354	Intermediate Similarity	NPC34056
0.8333	Intermediate Similarity	NPC268905
0.8333	Intermediate Similarity	NPC246164
0.8323	Intermediate Similarity	NPC56358
0.8313	Intermediate Similarity	NPC472771
0.8302	Intermediate Similarity	NPC62799
0.8291	Intermediate Similarity	NPC84479
0.8284	Intermediate Similarity	NPC255787
0.8284	Intermediate Similarity	NPC472652
0.8284	Intermediate Similarity	NPC327922
0.8269	Intermediate Similarity	NPC56197
0.8263	Intermediate Similarity	NPC476197
0.8263	Intermediate Similarity	NPC472773
0.8263	Intermediate Similarity	NPC472139
0.8261	Intermediate Similarity	NPC472654
0.8253	Intermediate Similarity	NPC191828
0.825	Intermediate Similarity	NPC221809
0.825	Intermediate Similarity	NPC471174
0.825	Intermediate Similarity	NPC470941
0.8242	Intermediate Similarity	NPC299038
0.8239	Intermediate Similarity	NPC56731
0.8232	Intermediate Similarity	NPC92979
0.8228	Intermediate Similarity	NPC80635
0.8228	Intermediate Similarity	NPC205071
0.8225	Intermediate Similarity	NPC473766
0.8225	Intermediate Similarity	NPC472651
0.8225	Intermediate Similarity	NPC473753
0.8225	Intermediate Similarity	NPC476224
0.8221	Intermediate Similarity	NPC84063
0.8221	Intermediate Similarity	NPC33938
0.821	Intermediate Similarity	NPC476122
0.821	Intermediate Similarity	NPC196846
0.821	Intermediate Similarity	NPC470997
0.8199	Intermediate Similarity	NPC19747
0.8194	Intermediate Similarity	NPC307401
0.8193	Intermediate Similarity	NPC475967
0.8193	Intermediate Similarity	NPC123153
0.8187	Intermediate Similarity	NPC285227
0.8187	Intermediate Similarity	NPC471292
0.8182	Intermediate Similarity	NPC471169
0.8182	Intermediate Similarity	NPC204663
0.8182	Intermediate Similarity	NPC175964
0.8182	Intermediate Similarity	NPC126723
0.8176	Intermediate Similarity	NPC271235
0.8176	Intermediate Similarity	NPC251865
0.8165	Intermediate Similarity	NPC263337
0.8165	Intermediate Similarity	NPC121158
0.8148	Intermediate Similarity	NPC211625
0.8148	Intermediate Similarity	NPC234494
0.8148	Intermediate Similarity	NPC195325
0.8144	Intermediate Similarity	NPC472653
0.8144	Intermediate Similarity	NPC472299
0.8136	Intermediate Similarity	NPC472662
0.8136	Intermediate Similarity	NPC472663
0.8133	Intermediate Similarity	NPC472772
0.8133	Intermediate Similarity	NPC195131
0.8133	Intermediate Similarity	NPC472283
0.8133	Intermediate Similarity	NPC81405
0.8129	Intermediate Similarity	NPC470995
0.8125	Intermediate Similarity	NPC5676
0.8121	Intermediate Similarity	NPC471175
0.8118	Intermediate Similarity	NPC41689
0.8118	Intermediate Similarity	NPC472775
0.8118	Intermediate Similarity	NPC472764
0.8118	Intermediate Similarity	NPC472774
0.8113	Intermediate Similarity	NPC223415
0.811	Intermediate Similarity	NPC469503
0.8107	Intermediate Similarity	NPC261184
0.8098	Intermediate Similarity	NPC159927
0.8098	Intermediate Similarity	NPC474305
0.8098	Intermediate Similarity	NPC469335
0.8095	Intermediate Similarity	NPC470939
0.8095	Intermediate Similarity	NPC82851
0.8095	Intermediate Similarity	NPC200782
0.8092	Intermediate Similarity	NPC148185
0.8092	Intermediate Similarity	NPC94763
0.8089	Intermediate Similarity	NPC473613
0.8089	Intermediate Similarity	NPC4341
0.8089	Intermediate Similarity	NPC473112
0.8089	Intermediate Similarity	NPC473085
0.8089	Intermediate Similarity	NPC48017
0.8089	Intermediate Similarity	NPC184747
0.8089	Intermediate Similarity	NPC200592
0.8089	Intermediate Similarity	NPC147880
0.8089	Intermediate Similarity	NPC43241
0.8089	Intermediate Similarity	NPC473758
0.8089	Intermediate Similarity	NPC473109
0.8089	Intermediate Similarity	NPC473060
0.8089	Intermediate Similarity	NPC202260
0.8089	Intermediate Similarity	NPC476094

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 NPC126984 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	843
0.2-0.3	1596
0.3-0.4	2687
0.4-0.5	2214
0.5-0.6	1037
0.6-0.7	382
0.7-0.8	42
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
0.8229	Intermediate Similarity	NPD8434	Phase 2
0.7904	Intermediate Similarity	NPD5760	Phase 2
0.7904	Intermediate Similarity	NPD5761	Phase 2
0.7824	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6764	Approved
0.774	Intermediate Similarity	NPD6765	Approved
0.7716	Intermediate Similarity	NPD4628	Phase 3
0.7667	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD8127	Discontinued
0.759	Intermediate Similarity	NPD6273	Approved
0.7588	Intermediate Similarity	NPD7819	Suspended
0.7569	Intermediate Similarity	NPD6784	Approved
0.7569	Intermediate Similarity	NPD6785	Approved
0.7472	Intermediate Similarity	NPD5844	Phase 1
0.7471	Intermediate Similarity	NPD5494	Approved
0.744	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD920	Approved
0.7414	Intermediate Similarity	NPD919	Approved
0.7412	Intermediate Similarity	NPD6599	Discontinued
0.7399	Intermediate Similarity	NPD4966	Approved
0.7399	Intermediate Similarity	NPD4965	Approved
0.7399	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4967	Phase 2
0.7384	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7075	Discontinued
0.7348	Intermediate Similarity	NPD6559	Discontinued
0.7333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7199	Phase 2
0.7321	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6234	Discontinued
0.7312	Intermediate Similarity	NPD8032	Phase 2
0.7305	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7473	Discontinued
0.7256	Intermediate Similarity	NPD2796	Approved
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.7247	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3817	Phase 2
0.7241	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD37	Approved
0.7225	Intermediate Similarity	NPD6801	Discontinued
0.7195	Intermediate Similarity	NPD3748	Approved
0.7191	Intermediate Similarity	NPD6232	Discontinued
0.7168	Intermediate Similarity	NPD7411	Suspended
0.7164	Intermediate Similarity	NPD8404	Phase 2
0.716	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6799	Approved
0.7151	Intermediate Similarity	NPD3226	Approved
0.7135	Intermediate Similarity	NPD1247	Approved
0.7127	Intermediate Similarity	NPD7799	Discontinued
0.7127	Intermediate Similarity	NPD7228	Approved
0.7127	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1243	Approved
0.7125	Intermediate Similarity	NPD6832	Phase 2
0.7108	Intermediate Similarity	NPD1471	Phase 3
0.7104	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7768	Phase 2
0.7101	Intermediate Similarity	NPD7236	Approved
0.7097	Intermediate Similarity	NPD17	Approved
0.7091	Intermediate Similarity	NPD2799	Discontinued
0.7086	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8312	Approved
0.7081	Intermediate Similarity	NPD8313	Approved
0.7077	Intermediate Similarity	NPD7497	Discontinued
0.7065	Intermediate Similarity	NPD7685	Pre-registration
0.7062	Intermediate Similarity	NPD3749	Approved
0.7056	Intermediate Similarity	NPD3926	Phase 2
0.7052	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2438	Suspended
0.7037	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3818	Discontinued
0.7029	Intermediate Similarity	NPD1934	Approved
0.7017	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6355	Discontinued
0.7011	Intermediate Similarity	NPD4380	Phase 2
0.7006	Intermediate Similarity	NPD6002	Phase 3
0.7006	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6005	Phase 3
0.7006	Intermediate Similarity	NPD6004	Phase 3
0.7	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7239	Suspended
0.6989	Remote Similarity	NPD8455	Phase 2
0.6982	Remote Similarity	NPD7003	Approved
0.6982	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7240	Approved
0.6966	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3972	Approved
0.6962	Remote Similarity	NPD1608	Approved
0.6951	Remote Similarity	NPD4140	Approved
0.6949	Remote Similarity	NPD5402	Approved
0.6949	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1551	Phase 2
0.6944	Remote Similarity	NPD6959	Discontinued
0.6936	Remote Similarity	NPD5403	Approved
0.6923	Remote Similarity	NPD6166	Phase 2
0.6923	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5401	Approved
0.6919	Remote Similarity	NPD2533	Approved
0.6919	Remote Similarity	NPD2532	Approved
0.6919	Remote Similarity	NPD2534	Approved
0.6919	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5327	Phase 3
0.691	Remote Similarity	NPD3882	Suspended
0.6905	Remote Similarity	NPD2346	Discontinued
0.6905	Remote Similarity	NPD5763	Approved
0.6905	Remote Similarity	NPD5762	Approved
0.6902	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD1465	Phase 2
0.6882	Remote Similarity	NPD4110	Phase 3
0.6882	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6385	Approved
0.6875	Remote Similarity	NPD6386	Approved
0.6871	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7074	Phase 3
0.6864	Remote Similarity	NPD1549	Phase 2
0.6848	Remote Similarity	NPD4307	Phase 2
0.6848	Remote Similarity	NPD2979	Phase 3
0.6845	Remote Similarity	NPD6099	Approved
0.6845	Remote Similarity	NPD6100	Approved
0.6842	Remote Similarity	NPD3887	Approved
0.6837	Remote Similarity	NPD4107	Approved
0.6832	Remote Similarity	NPD3267	Approved
0.6832	Remote Similarity	NPD3266	Approved
0.6829	Remote Similarity	NPD6798	Discontinued
0.6829	Remote Similarity	NPD3764	Approved
0.6821	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5585	Approved
0.6811	Remote Similarity	NPD7054	Approved
0.6807	Remote Similarity	NPD5735	Approved
0.6807	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1933	Approved
0.6805	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD2801	Approved
0.679	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8150	Discontinued
0.6788	Remote Similarity	NPD6233	Phase 2
0.6788	Remote Similarity	NPD6663	Approved
0.6786	Remote Similarity	NPD7033	Discontinued
0.6784	Remote Similarity	NPD8166	Discontinued
0.6776	Remote Similarity	NPD5242	Approved
0.6774	Remote Similarity	NPD7472	Approved
0.677	Remote Similarity	NPD1876	Approved
0.6768	Remote Similarity	NPD7095	Approved
0.6765	Remote Similarity	NPD970	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5353	Approved
0.6757	Remote Similarity	NPD7177	Discontinued
0.6755	Remote Similarity	NPD7808	Phase 3
0.6746	Remote Similarity	NPD2935	Discontinued
0.6744	Remote Similarity	NPD6190	Approved
0.6728	Remote Similarity	NPD2797	Approved
0.6727	Remote Similarity	NPD3268	Approved
0.6727	Remote Similarity	NPD2313	Discontinued
0.6726	Remote Similarity	NPD7097	Phase 1
0.6723	Remote Similarity	NPD7028	Phase 2
0.6721	Remote Similarity	NPD6808	Phase 2
0.6717	Remote Similarity	NPD4482	Phase 3
0.6706	Remote Similarity	NPD2344	Approved
0.6702	Remote Similarity	NPD7251	Discontinued
0.6701	Remote Similarity	NPD8285	Discontinued
0.6687	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1281	Approved
0.6686	Remote Similarity	NPD1510	Phase 2
0.6686	Remote Similarity	NPD4308	Phase 3
0.6685	Remote Similarity	NPD6873	Phase 2
0.6684	Remote Similarity	NPD8407	Phase 2
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6653	Approved
0.665	Remote Similarity	NPD7680	Approved
0.6649	Remote Similarity	NPD6797	Phase 2
0.6649	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4476	Approved
0.6647	Remote Similarity	NPD4477	Approved
0.6646	Remote Similarity	NPD5736	Approved
0.663	Remote Similarity	NPD7058	Phase 2
0.663	Remote Similarity	NPD7057	Phase 3
0.663	Remote Similarity	NPD7315	Approved
0.6628	Remote Similarity	NPD2800	Approved
0.6618	Remote Similarity	NPD7047	Phase 3
0.6614	Remote Similarity	NPD8368	Discontinued
0.6608	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2353	Approved
0.6605	Remote Similarity	NPD4359	Approved
0.6592	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1512	Approved
0.6585	Remote Similarity	NPD2798	Approved
0.6584	Remote Similarity	NPD7999	Approved
0.6578	Remote Similarity	NPD3751	Discontinued
0.657	Remote Similarity	NPD2897	Discontinued
0.6568	Remote Similarity	NPD6353	Approved
0.6568	Remote Similarity	NPD1607	Approved
0.6567	Remote Similarity	NPD7435	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data