NPASS Compound

Structure

CID326084 OpenBabel06191716182D 52 57 0 0 1 0 0 0 0 0999 V2000 1.5160 -3.5762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1094 -3.3900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6730 -0.6923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7022 -0.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5810 -1.0684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5533 -1.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4653 -3.8306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5533 1.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5533 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7022 1.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9129 1.7864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1333 1.1881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2882 2.2307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8511 -2.4569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1602 -3.1357 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.5447 0.2820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8511 -1.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8209 1.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5085 1.6325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7022 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2615 0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8511 -1.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8511 1.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1961 1.8547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6368 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3244 0.8803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8511 -2.4569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9492 0.4360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8511 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6006 2.0086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1695 -0.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8571 0.0599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9058 -2.1864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2324 0.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7022 -2.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7022 -0.9828 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 1.9655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9758 2.4529 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.9310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4723 2.9829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2978 -1.1367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9854 -0.9145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8511 0.4914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6007 -1.4915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0120 1.1025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7022 -3.9310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3606 -0.4701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5533 -2.4569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9565 -1.9320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 50 1 0 0 0 0 6 51 1 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 20 1 0 0 0 0 10 23 2 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 21 1 0 0 0 0 13 19 2 0 0 0 0 13 24 1 0 0 0 0 14 22 2 0 0 0 0 14 25 1 0 0 0 0 15 36 1 0 0 0 0 16 26 2 0 0 0 0 16 28 1 0 0 0 0 17 27 2 0 0 0 0 17 29 1 0 0 0 0 18 30 2 0 0 0 0 18 32 1 0 0 0 0 19 26 1 0 0 0 0 19 32 1 0 0 0 0 20 31 2 0 0 0 0 20 39 1 0 0 0 0 21 33 2 0 0 0 0 21 39 1 0 0 0 0 22 27 1 0 0 0 0 22 39 1 0 0 0 0 23 31 1 0 0 0 0 23 40 1 0 0 0 0 24 28 2 0 0 0 0 24 41 1 0 0 0 0 25 29 2 0 0 0 0 25 42 1 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 28 37 1 0 0 0 0 29 38 1 0 0 0 0 30 33 1 0 0 0 0 30 34 1 0 0 0 0 31 35 1 0 0 0 0 32 43 2 0 0 0 0 33 44 1 0 0 0 0 34 45 2 0 0 0 0 35 46 2 0 0 0 0 36 47 2 0 0 0 0 36 52 1 0 0 0 0 37 48 2 0 0 0 0 37 50 1 0 0 0 0 38 49 2 0 0 0 0 38 51 1 0 0 0 0 39 52 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	708.18
Volume:	698.578
LogP:	6.335
LogD:	2.398
LogS:	-4.3
# Rotatable Bonds:	9
TPSA:	211.03
# H-Bond Aceptor:	13
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.137
Synthetic Accessibility Score:	4.351
Fsp3:	0.231
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.031
MDCK Permeability:	1.3274867342261132e-05
Pgp-inhibitor:	0.863
Pgp-substrate:	0.052
Human Intestinal Absorption (HIA):	0.859
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	101.0243148803711%
Volume Distribution (VD):	0.165
Pgp-substrate:	1.1396294832229614%

ADMET: Metabolism

CYP1A2-inhibitor:	0.206
CYP1A2-substrate:	0.877
CYP2C19-inhibitor:	0.607
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.772
CYP2C9-substrate:	0.432
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.28
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	1.464
Half-life (T1/2):	0.005

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.444
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.062
Carcinogencity:	0.258
Eye Corrosion:	0.003
Eye Irritation:	0.91
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC326084

Natural Product ID:	NPC326084
*Common Name:**	Scutianthraquinone A
IUPAC Name:	methyl 7-[2,5-dihydroxy-3-methoxycarbonyl-4-methyl-9-(2-methylbutanoyloxy)-10-oxoanthracen-9-yl]-3,8-dihydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylate
Synonyms:
Standard InCHIKey:	LUBCWELSQUOSLN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C39H32O13/c1-7-15(2)36(47)52-39(20-9-8-10-23(40)31(20)35(46)27-17(4)29(38(49)51-6)25(42)14-22(27)39)21-12-11-18-30(33(21)44)34(45)26-16(3)28(37(48)50-5)24(41)13-19(26)32(18)43/h8-15,40-42,44H,7H2,1-6H3
SMILES:	CCC(C(=O)OC1(c2ccc3c(c2O)C(=O)c2c(C3=O)cc(c(c2C)C(=O)OC)O)c2cccc(c2C(=O)c2c1cc(O)c(c2C)C(=O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453764
PubChem CID:	44156991
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0001911] Anthracenecarboxylic acids and derivatives [CHEMONTID:0002424] Anthracenecarboxylic acids

*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
NPO1248	Scutia myrtina	Species	Rhamnaceae	Eukaryota	roots	n.a.	n.a.	PMID[17378532]
NPO1248	Scutia myrtina	Species	Rhamnaceae	Eukaryota	n.a.	Madagascar forest	n.a.	PMID[19282186]
NPO1248	Scutia myrtina	Species	Rhamnaceae	Eukaryota	n.a.	bark	n.a.	PMID[19282186]
NPO1248	Scutia myrtina	Species	Rhamnaceae	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	2

Activity Type	# Activity
Cell Line	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	7600.0	nM	PMID[545362]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1230.0	nM	PMID[545362]
NPT2	Others	Unspecified		Ratio IC50	=	6.1	n.a.	PMID[545362]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1200.0	nM	PMID[545362]
NPT2	Others	Unspecified		Ratio IC50	=	6.3	n.a.	PMID[545362]

☑ 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 NPC326084 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	368
0.1-0.2	1561
0.2-0.3	3323
0.3-0.4	8001
0.4-0.5	10794
0.5-0.6	4868
0.6-0.7	6874
0.7-0.8	6408
0.8-0.85	437
0.85-0.9	57
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC475449
0.9933	High Similarity	NPC317580
0.98	High Similarity	NPC318270
0.9067	High Similarity	NPC66593
0.8917	High Similarity	NPC66029
0.8903	High Similarity	NPC315520
0.8903	High Similarity	NPC205766
0.8889	High Similarity	NPC314437
0.8889	High Similarity	NPC147250
0.8831	High Similarity	NPC119767
0.8816	High Similarity	NPC471682
0.875	High Similarity	NPC257644
0.8742	High Similarity	NPC474861
0.8733	High Similarity	NPC4214
0.8701	High Similarity	NPC471683
0.8696	High Similarity	NPC472060
0.8696	High Similarity	NPC472052
0.8696	High Similarity	NPC470342
0.8675	High Similarity	NPC477836
0.8659	High Similarity	NPC477835
0.8627	High Similarity	NPC19631
0.8627	High Similarity	NPC239136
0.8618	High Similarity	NPC225243
0.8616	High Similarity	NPC470408
0.8616	High Similarity	NPC182921
0.8616	High Similarity	NPC218870
0.8616	High Similarity	NPC474622
0.8616	High Similarity	NPC474621
0.8616	High Similarity	NPC474824
0.8606	High Similarity	NPC76647
0.859	High Similarity	NPC37709
0.8589	High Similarity	NPC315772
0.858	High Similarity	NPC476506
0.8571	High Similarity	NPC263483
0.8571	High Similarity	NPC53016
0.8571	High Similarity	NPC296752
0.8553	High Similarity	NPC474534
0.8553	High Similarity	NPC474533
0.8533	High Similarity	NPC80035
0.8528	High Similarity	NPC472261
0.8526	High Similarity	NPC85393
0.8526	High Similarity	NPC110882
0.8526	High Similarity	NPC271944
0.8497	Intermediate Similarity	NPC315578
0.8487	Intermediate Similarity	NPC13715
0.8485	Intermediate Similarity	NPC71390
0.8481	Intermediate Similarity	NPC477221
0.8471	Intermediate Similarity	NPC478018
0.8462	Intermediate Similarity	NPC478019
0.8452	Intermediate Similarity	NPC474203
0.8452	Intermediate Similarity	NPC293545
0.8452	Intermediate Similarity	NPC174905
0.8452	Intermediate Similarity	NPC295712
0.8452	Intermediate Similarity	NPC451542
0.8452	Intermediate Similarity	NPC313047
0.8447	Intermediate Similarity	NPC66508
0.8447	Intermediate Similarity	NPC226656
0.8431	Intermediate Similarity	NPC26924
0.8408	Intermediate Similarity	NPC470570
0.8405	Intermediate Similarity	NPC324736
0.8397	Intermediate Similarity	NPC21599
0.8397	Intermediate Similarity	NPC193703
0.8397	Intermediate Similarity	NPC227841
0.8393	Intermediate Similarity	NPC478021
0.8387	Intermediate Similarity	NPC69755
0.8387	Intermediate Similarity	NPC193555
0.8377	Intermediate Similarity	NPC168471
0.8373	Intermediate Similarity	NPC478020
0.8373	Intermediate Similarity	NPC478022
0.8364	Intermediate Similarity	NPC97637
0.8364	Intermediate Similarity	NPC187934
0.8354	Intermediate Similarity	NPC290194
0.8353	Intermediate Similarity	NPC477991
0.8353	Intermediate Similarity	NPC477992
0.8353	Intermediate Similarity	NPC70862
0.8344	Intermediate Similarity	NPC34482
0.8344	Intermediate Similarity	NPC67197
0.8343	Intermediate Similarity	NPC294501
0.8333	Intermediate Similarity	NPC266469
0.8333	Intermediate Similarity	NPC175477
0.8323	Intermediate Similarity	NPC30027
0.8323	Intermediate Similarity	NPC290550
0.8313	Intermediate Similarity	NPC476505
0.8313	Intermediate Similarity	NPC477914
0.8303	Intermediate Similarity	NPC273467
0.8303	Intermediate Similarity	NPC189552
0.8301	Intermediate Similarity	NPC62272
0.8291	Intermediate Similarity	NPC143685
0.8282	Intermediate Similarity	NPC478027
0.8282	Intermediate Similarity	NPC146211
0.8282	Intermediate Similarity	NPC474360
0.828	Intermediate Similarity	NPC48762
0.8278	Intermediate Similarity	NPC225051
0.8278	Intermediate Similarity	NPC472591
0.8274	Intermediate Similarity	NPC286230
0.8274	Intermediate Similarity	NPC324522
0.8274	Intermediate Similarity	NPC105414
0.8274	Intermediate Similarity	NPC234497
0.8274	Intermediate Similarity	NPC253730
0.8274	Intermediate Similarity	NPC470341
0.8274	Intermediate Similarity	NPC107009
0.8274	Intermediate Similarity	NPC472058
0.8269	Intermediate Similarity	NPC85310
0.8261	Intermediate Similarity	NPC477276
0.8258	Intermediate Similarity	NPC181560
0.8258	Intermediate Similarity	NPC169452
0.8256	Intermediate Similarity	NPC478000
0.8242	Intermediate Similarity	NPC312993
0.8242	Intermediate Similarity	NPC284495
0.8242	Intermediate Similarity	NPC185617
0.8242	Intermediate Similarity	NPC186325
0.8239	Intermediate Similarity	NPC10842
0.8235	Intermediate Similarity	NPC473113
0.8235	Intermediate Similarity	NPC183441
0.8235	Intermediate Similarity	NPC155211
0.8232	Intermediate Similarity	NPC208258
0.8228	Intermediate Similarity	NPC12402
0.8224	Intermediate Similarity	NPC161964
0.8224	Intermediate Similarity	NPC287604
0.8224	Intermediate Similarity	NPC472262
0.8224	Intermediate Similarity	NPC288089
0.8221	Intermediate Similarity	NPC472807
0.8221	Intermediate Similarity	NPC37253
0.8221	Intermediate Similarity	NPC471456
0.8221	Intermediate Similarity	NPC79375
0.8221	Intermediate Similarity	NPC3898
0.8218	Intermediate Similarity	NPC473717
0.8218	Intermediate Similarity	NPC293227
0.8218	Intermediate Similarity	NPC475662
0.8218	Intermediate Similarity	NPC473631
0.8214	Intermediate Similarity	NPC251336
0.8208	Intermediate Similarity	NPC72783
0.8208	Intermediate Similarity	NPC473785
0.8205	Intermediate Similarity	NPC246638
0.8204	Intermediate Similarity	NPC473009
0.8194	Intermediate Similarity	NPC138099
0.8194	Intermediate Similarity	NPC242994
0.8193	Intermediate Similarity	NPC137232
0.8193	Intermediate Similarity	NPC18380
0.8187	Intermediate Similarity	NPC221352
0.8187	Intermediate Similarity	NPC172329
0.8187	Intermediate Similarity	NPC152233
0.8187	Intermediate Similarity	NPC2569
0.8187	Intermediate Similarity	NPC65118
0.8187	Intermediate Similarity	NPC472054
0.8182	Intermediate Similarity	NPC474373
0.8182	Intermediate Similarity	NPC55443
0.8182	Intermediate Similarity	NPC18699
0.8182	Intermediate Similarity	NPC177650
0.8171	Intermediate Similarity	NPC56049
0.8171	Intermediate Similarity	NPC54830
0.8165	Intermediate Similarity	NPC10764
0.8165	Intermediate Similarity	NPC79627
0.816	Intermediate Similarity	NPC208806
0.816	Intermediate Similarity	NPC477691
0.816	Intermediate Similarity	NPC324447
0.816	Intermediate Similarity	NPC214632
0.8158	Intermediate Similarity	NPC115458
0.8158	Intermediate Similarity	NPC52407
0.8158	Intermediate Similarity	NPC43627
0.8158	Intermediate Similarity	NPC53896
0.8155	Intermediate Similarity	NPC469664
0.8155	Intermediate Similarity	NPC473010
0.8155	Intermediate Similarity	NPC169471
0.8153	Intermediate Similarity	NPC469520
0.815	Intermediate Similarity	NPC207467
0.8148	Intermediate Similarity	NPC35
0.8144	Intermediate Similarity	NPC15374
0.8144	Intermediate Similarity	NPC473012
0.8141	Intermediate Similarity	NPC275903
0.8137	Intermediate Similarity	NPC474310
0.8137	Intermediate Similarity	NPC247219
0.8137	Intermediate Similarity	NPC327962
0.8137	Intermediate Similarity	NPC329933
0.8133	Intermediate Similarity	NPC184326
0.8133	Intermediate Similarity	NPC195136
0.8133	Intermediate Similarity	NPC121647
0.8133	Intermediate Similarity	NPC226462
0.8133	Intermediate Similarity	NPC98023
0.8133	Intermediate Similarity	NPC292863
0.8129	Intermediate Similarity	NPC478002
0.8125	Intermediate Similarity	NPC475352
0.8125	Intermediate Similarity	NPC126767
0.8125	Intermediate Similarity	NPC325032
0.8125	Intermediate Similarity	NPC289042
0.8125	Intermediate Similarity	NPC475348
0.8125	Intermediate Similarity	NPC125801
0.8125	Intermediate Similarity	NPC261271
0.8125	Intermediate Similarity	NPC190648
0.8125	Intermediate Similarity	NPC475220
0.8125	Intermediate Similarity	NPC312929
0.8125	Intermediate Similarity	NPC473686
0.8125	Intermediate Similarity	NPC477483
0.8125	Intermediate Similarity	NPC56433
0.8125	Intermediate Similarity	NPC245584
0.8125	Intermediate Similarity	NPC118027
0.8125	Intermediate Similarity	NPC221140
0.8125	Intermediate Similarity	NPC229817
0.8121	Intermediate Similarity	NPC318527
0.8121	Intermediate Similarity	NPC324358

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 NPC326084 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	986
0.2-0.3	1464
0.3-0.4	2588
0.4-0.5	2141
0.5-0.6	1111
0.6-0.7	376
0.7-0.8	142
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8397	Intermediate Similarity	NPD7390	Discontinued
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8301	Intermediate Similarity	NPD5406	Approved
0.8301	Intermediate Similarity	NPD5405	Approved
0.8301	Intermediate Similarity	NPD5404	Approved
0.8301	Intermediate Similarity	NPD5408	Approved
0.825	Intermediate Similarity	NPD3226	Approved
0.8155	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6232	Discontinued
0.8092	Intermediate Similarity	NPD8313	Approved
0.8092	Intermediate Similarity	NPD8312	Approved
0.8089	Intermediate Similarity	NPD7003	Approved
0.8084	Intermediate Similarity	NPD6959	Discontinued
0.8079	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD8150	Discontinued
0.8049	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD2935	Discontinued
0.7927	Intermediate Similarity	NPD7411	Suspended
0.7914	Intermediate Similarity	NPD7458	Discontinued
0.7898	Intermediate Similarity	NPD2346	Discontinued
0.7844	Intermediate Similarity	NPD7768	Phase 2
0.7778	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD8166	Discontinued
0.7701	Intermediate Similarity	NPD8320	Phase 1
0.7701	Intermediate Similarity	NPD8319	Approved
0.7697	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3749	Approved
0.7688	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2533	Approved
0.7669	Intermediate Similarity	NPD2534	Approved
0.7669	Intermediate Similarity	NPD2532	Approved
0.7669	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2799	Discontinued
0.7632	Intermediate Similarity	NPD1470	Approved
0.7613	Intermediate Similarity	NPD3764	Approved
0.7606	Intermediate Similarity	NPD7870	Phase 2
0.7606	Intermediate Similarity	NPD7871	Phase 2
0.7568	Intermediate Similarity	NPD7699	Phase 2
0.7568	Intermediate Similarity	NPD7700	Phase 2
0.7553	Intermediate Similarity	NPD7435	Discontinued
0.7539	Intermediate Similarity	NPD8151	Discontinued
0.7516	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.746	Intermediate Similarity	NPD7698	Approved
0.746	Intermediate Similarity	NPD7696	Phase 3
0.746	Intermediate Similarity	NPD7697	Approved
0.7455	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4380	Phase 2
0.7409	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7874	Approved
0.7394	Intermediate Similarity	NPD6781	Approved
0.7394	Intermediate Similarity	NPD6776	Approved
0.7394	Intermediate Similarity	NPD6778	Approved
0.7394	Intermediate Similarity	NPD6779	Approved
0.7394	Intermediate Similarity	NPD6777	Approved
0.7394	Intermediate Similarity	NPD6780	Approved
0.7394	Intermediate Similarity	NPD6782	Approved
0.7389	Intermediate Similarity	NPD2313	Discontinued
0.7368	Intermediate Similarity	NPD1201	Approved
0.7351	Intermediate Similarity	NPD6212	Phase 3
0.7351	Intermediate Similarity	NPD6213	Phase 3
0.7351	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2344	Approved
0.7326	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3750	Approved
0.7312	Intermediate Similarity	NPD1607	Approved
0.731	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7701	Phase 2
0.7305	Intermediate Similarity	NPD6273	Approved
0.729	Intermediate Similarity	NPD1164	Approved
0.7282	Intermediate Similarity	NPD7801	Approved
0.7278	Intermediate Similarity	NPD3268	Approved
0.7267	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD8285	Discontinued
0.7247	Intermediate Similarity	NPD7177	Discontinued
0.7232	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6166	Phase 2
0.7226	Intermediate Similarity	NPD1283	Approved
0.7222	Intermediate Similarity	NPD1510	Phase 2
0.7222	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9493	Approved
0.7194	Intermediate Similarity	NPD7783	Phase 2
0.7194	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1240	Approved
0.7182	Intermediate Similarity	NPD6559	Discontinued
0.7174	Intermediate Similarity	NPD8434	Phase 2
0.7169	Intermediate Similarity	NPD2309	Approved
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7151	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6801	Discontinued
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6599	Discontinued
0.7135	Intermediate Similarity	NPD6823	Phase 2
0.7134	Intermediate Similarity	NPD2798	Approved
0.7134	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1471	Phase 3
0.7126	Intermediate Similarity	NPD7236	Approved
0.7119	Intermediate Similarity	NPD5710	Approved
0.7119	Intermediate Similarity	NPD5711	Approved
0.7118	Intermediate Similarity	NPD7239	Suspended
0.7117	Intermediate Similarity	NPD4308	Phase 3
0.7113	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2801	Approved
0.7108	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7008	Discontinued
0.7102	Intermediate Similarity	NPD5494	Approved
0.7091	Intermediate Similarity	NPD1549	Phase 2
0.7086	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD943	Approved
0.7081	Intermediate Similarity	NPD2979	Phase 3
0.7072	Intermediate Similarity	NPD7074	Phase 3
0.707	Intermediate Similarity	NPD1203	Approved
0.7069	Intermediate Similarity	NPD3817	Phase 2
0.7052	Intermediate Similarity	NPD1934	Approved
0.7033	Intermediate Similarity	NPD5953	Discontinued
0.7032	Intermediate Similarity	NPD1281	Approved
0.703	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3300	Phase 2
0.7022	Intermediate Similarity	NPD7229	Phase 3
0.7019	Intermediate Similarity	NPD6663	Approved
0.7017	Intermediate Similarity	NPD7054	Approved
0.7013	Intermediate Similarity	NPD4626	Approved
0.7012	Intermediate Similarity	NPD3748	Approved
0.7011	Intermediate Similarity	NPD8455	Phase 2
0.7011	Intermediate Similarity	NPD1465	Phase 2
0.7006	Intermediate Similarity	NPD4628	Phase 3
0.7	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1511	Approved
0.6982	Remote Similarity	NPD6799	Approved
0.6981	Remote Similarity	NPD5736	Approved
0.6978	Remote Similarity	NPD7472	Approved
0.6971	Remote Similarity	NPD5402	Approved
0.697	Remote Similarity	NPD2438	Suspended
0.697	Remote Similarity	NPD2796	Approved
0.697	Remote Similarity	NPD1551	Phase 2
0.697	Remote Similarity	NPD6100	Approved
0.697	Remote Similarity	NPD6099	Approved
0.6964	Remote Similarity	NPD6190	Approved
0.6962	Remote Similarity	NPD2797	Approved
0.6962	Remote Similarity	NPD3267	Approved
0.6962	Remote Similarity	NPD3266	Approved
0.6961	Remote Similarity	NPD3818	Discontinued
0.6957	Remote Similarity	NPD411	Approved
0.6957	Remote Similarity	NPD7808	Phase 3
0.6951	Remote Similarity	NPD7097	Phase 1
0.6933	Remote Similarity	NPD230	Phase 1
0.6933	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD447	Suspended
0.6932	Remote Similarity	NPD3882	Suspended
0.6923	Remote Similarity	NPD7286	Phase 2
0.6914	Remote Similarity	NPD8032	Phase 2
0.6909	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3019	Approved
0.6902	Remote Similarity	NPD7251	Discontinued
0.6901	Remote Similarity	NPD1512	Approved
0.689	Remote Similarity	NPD6651	Approved
0.6889	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD9545	Approved
0.6879	Remote Similarity	NPD3972	Approved
0.6879	Remote Similarity	NPD9717	Approved
0.6872	Remote Similarity	NPD8127	Discontinued
0.6871	Remote Similarity	NPD4060	Phase 1
0.6871	Remote Similarity	NPD4307	Phase 2
0.6868	Remote Similarity	NPD7228	Approved
0.6868	Remote Similarity	NPD3751	Discontinued
0.6865	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.686	Remote Similarity	NPD920	Approved
0.6857	Remote Similarity	NPD37	Approved
0.6856	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6234	Discontinued
0.6848	Remote Similarity	NPD6797	Phase 2
0.6845	Remote Similarity	NPD2800	Approved
0.6842	Remote Similarity	NPD5951	Approved
0.6839	Remote Similarity	NPD6585	Discontinued
0.6839	Remote Similarity	NPD1651	Approved
0.6839	Remote Similarity	NPD5691	Approved
0.6836	Remote Similarity	NPD4967	Phase 2
0.6836	Remote Similarity	NPD4966	Approved
0.6836	Remote Similarity	NPD4965	Approved
0.6833	Remote Similarity	NPD6808	Phase 2
0.6825	Remote Similarity	NPD4287	Approved
0.6811	Remote Similarity	NPD7685	Pre-registration
0.681	Remote Similarity	NPD7961	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