NPASS Compound

Structure

CID317580 OpenBabel06191716142D 51 56 0 0 1 0 0 0 0 0999 V2000 -2.4645 -3.8294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1082 -3.3890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6707 -0.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7017 -0.9825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2654 -0.8459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4033 -2.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5525 1.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5525 0.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7017 1.9649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9117 1.7858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1323 1.1878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2859 2.2301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 -2.4561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1592 -3.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5424 0.2820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8508 -1.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8194 1.4099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5065 1.6320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7017 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2605 0.2137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 -1.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 1.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1936 1.8541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6347 0.6579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3219 0.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8508 -2.4561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9476 0.4358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 0.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5988 2.0080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1682 -0.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8553 0.0598 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 -2.9049 -2.1857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2295 0.5041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7017 -2.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7017 -0.9825 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 1.9649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9731 2.4522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.9298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4706 2.9820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2964 -1.1363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9835 -0.9142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8508 0.4912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5996 -1.4910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0090 1.1022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7017 -3.9298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3578 -0.4700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5525 -2.4561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9559 -1.9314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 49 1 0 0 0 0 6 50 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 19 1 0 0 0 0 9 22 2 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 18 2 0 0 0 0 12 23 1 0 0 0 0 13 21 2 0 0 0 0 13 24 1 0 0 0 0 14 35 1 0 0 0 0 15 25 2 0 0 0 0 15 27 1 0 0 0 0 16 26 2 0 0 0 0 16 28 1 0 0 0 0 17 29 2 0 0 0 0 17 31 1 0 0 0 0 18 25 1 0 0 0 0 18 31 1 0 0 0 0 19 30 2 0 0 0 0 19 38 1 0 0 0 0 20 32 2 0 0 0 0 20 38 1 0 0 0 0 21 26 1 0 0 0 0 21 38 1 0 0 0 0 22 30 1 0 0 0 0 22 39 1 0 0 0 0 23 27 2 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 33 1 0 0 0 0 26 34 1 0 0 0 0 27 36 1 0 0 0 0 28 37 1 0 0 0 0 29 32 1 0 0 0 0 29 33 1 0 0 0 0 30 34 1 0 0 0 0 31 42 2 0 0 0 0 32 43 1 0 0 0 0 33 44 2 0 0 0 0 34 45 2 0 0 0 0 35 46 2 0 0 0 0 35 51 1 0 0 0 0 36 47 2 0 0 0 0 36 49 1 0 0 0 0 37 48 2 0 0 0 0 37 50 1 0 0 0 0 38 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	694.17
Volume:	681.282
LogP:	6.085
LogD:	2.3
LogS:	-4.339
# Rotatable Bonds:	8
TPSA:	211.03
# H-Bond Aceptor:	13
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.148
Synthetic Accessibility Score:	4.072
Fsp3:	0.211
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:	-6.08
MDCK Permeability:	1.5740330127300695e-05
Pgp-inhibitor:	0.842
Pgp-substrate:	0.062
Human Intestinal Absorption (HIA):	0.829
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	100.38306427001953%
Volume Distribution (VD):	0.158
Pgp-substrate:	1.4710787534713745%

ADMET: Metabolism

CYP1A2-inhibitor:	0.2
CYP1A2-substrate:	0.848
CYP2C19-inhibitor:	0.519
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.751
CYP2C9-substrate:	0.373
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.252
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	1.39
Half-life (T1/2):	0.006

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.066
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.463
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.067
Carcinogencity:	0.405
Eye Corrosion:	0.003
Eye Irritation:	0.905
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: NPC317580

Natural Product ID:	NPC317580
*Common Name:**	Scutianthraquinone B
IUPAC Name:	methyl 7-[2,5-dihydroxy-3-methoxycarbonyl-4-methyl-9-(2-methylpropanoyloxy)-10-oxoanthracen-9-yl]-3,8-dihydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylate
Synonyms:
Standard InCHIKey:	OWDCXJMCKGCGEQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C38H30O13/c1-14(2)35(46)51-38(19-8-7-9-22(39)30(19)34(45)26-16(4)28(37(48)50-6)24(41)13-21(26)38)20-11-10-17-29(32(20)43)33(44)25-15(3)27(36(47)49-5)23(40)12-18(25)31(17)42/h7-14,39-41,43H,1-6H3
SMILES:	CC1=C2C(=CC(=C1C(=O)OC)O)C(=O)C3=C(C2=O)C(=C(C=C3)C4(C5=C(C(=CC=C5)O)C(=O)C6=C(C(=C(C=C64)O)C(=O)OC)C)OC(=O)C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502755
PubChem CID:	44157016
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.	bark	n.a.	PMID[19282186]
NPO1248	Scutia myrtina	Species	Rhamnaceae	Eukaryota	n.a.	Madagascar forest	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	=	5800.0	nM	PMID[540448]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1140.0	nM	PMID[540448]
NPT2	Others	Unspecified		Ratio IC50	=	5.1	n.a.	PMID[540448]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5400.0	nM	PMID[540448]
NPT2	Others	Unspecified		Ratio IC50	=	1.1	n.a.	PMID[540448]

☑ 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 NPC317580 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
0.9933	High Similarity	NPC326084
0.9868	High Similarity	NPC475449
0.9866	High Similarity	NPC318270
0.9128	High Similarity	NPC66593
0.8974	High Similarity	NPC66029
0.8961	High Similarity	NPC315520
0.8961	High Similarity	NPC205766
0.8947	High Similarity	NPC147250
0.8947	High Similarity	NPC314437
0.8889	High Similarity	NPC119767
0.8874	High Similarity	NPC471682
0.8808	High Similarity	NPC257644
0.8797	High Similarity	NPC474861
0.8792	High Similarity	NPC4214
0.8758	High Similarity	NPC471683
0.875	High Similarity	NPC470342
0.875	High Similarity	NPC472052
0.875	High Similarity	NPC472060
0.8727	High Similarity	NPC477836
0.8712	High Similarity	NPC477835
0.8684	High Similarity	NPC239136
0.8684	High Similarity	NPC19631
0.8675	High Similarity	NPC225243
0.8671	High Similarity	NPC470408
0.8671	High Similarity	NPC218870
0.8671	High Similarity	NPC182921
0.8671	High Similarity	NPC474622
0.8671	High Similarity	NPC474621
0.8671	High Similarity	NPC474824
0.8645	High Similarity	NPC37709
0.8642	High Similarity	NPC315772
0.8627	High Similarity	NPC53016
0.8627	High Similarity	NPC296752
0.8625	High Similarity	NPC263483
0.8608	High Similarity	NPC474534
0.8608	High Similarity	NPC474533
0.8591	High Similarity	NPC80035
0.8553	High Similarity	NPC315578
0.8545	High Similarity	NPC76647
0.8543	High Similarity	NPC13715
0.8537	High Similarity	NPC71390
0.8535	High Similarity	NPC477221
0.8526	High Similarity	NPC478018
0.8519	High Similarity	NPC476506
0.8516	High Similarity	NPC478019
0.8506	High Similarity	NPC293545
0.8506	High Similarity	NPC313047
0.8506	High Similarity	NPC174905
0.8506	High Similarity	NPC474203
0.8506	High Similarity	NPC451542
0.8506	High Similarity	NPC295712
0.85	High Similarity	NPC226656
0.85	High Similarity	NPC66508
0.8487	Intermediate Similarity	NPC26924
0.8466	Intermediate Similarity	NPC472261
0.8462	Intermediate Similarity	NPC85393
0.8462	Intermediate Similarity	NPC271944
0.8462	Intermediate Similarity	NPC110882
0.8462	Intermediate Similarity	NPC470570
0.8457	Intermediate Similarity	NPC324736
0.8452	Intermediate Similarity	NPC227841
0.8452	Intermediate Similarity	NPC193703
0.8452	Intermediate Similarity	NPC21599
0.8443	Intermediate Similarity	NPC478021
0.8442	Intermediate Similarity	NPC69755
0.8442	Intermediate Similarity	NPC193555
0.8431	Intermediate Similarity	NPC168471
0.8424	Intermediate Similarity	NPC478020
0.8424	Intermediate Similarity	NPC478022
0.8415	Intermediate Similarity	NPC97637
0.8415	Intermediate Similarity	NPC187934
0.8408	Intermediate Similarity	NPC290194
0.8397	Intermediate Similarity	NPC34482
0.8395	Intermediate Similarity	NPC67197
0.8393	Intermediate Similarity	NPC294501
0.8385	Intermediate Similarity	NPC266469
0.8383	Intermediate Similarity	NPC175477
0.8377	Intermediate Similarity	NPC290550
0.8373	Intermediate Similarity	NPC30027
0.8365	Intermediate Similarity	NPC477914
0.8355	Intermediate Similarity	NPC62272
0.8354	Intermediate Similarity	NPC273467
0.8354	Intermediate Similarity	NPC189552
0.8333	Intermediate Similarity	NPC146211
0.8333	Intermediate Similarity	NPC48762
0.8333	Intermediate Similarity	NPC474360
0.8333	Intermediate Similarity	NPC478027
0.8333	Intermediate Similarity	NPC225051
0.8323	Intermediate Similarity	NPC472058
0.8323	Intermediate Similarity	NPC105414
0.8323	Intermediate Similarity	NPC324522
0.8323	Intermediate Similarity	NPC234497
0.8323	Intermediate Similarity	NPC470341
0.8323	Intermediate Similarity	NPC107009
0.8323	Intermediate Similarity	NPC85310
0.8313	Intermediate Similarity	NPC477276
0.8312	Intermediate Similarity	NPC181560
0.8312	Intermediate Similarity	NPC169452
0.8304	Intermediate Similarity	NPC478000
0.8294	Intermediate Similarity	NPC477992
0.8294	Intermediate Similarity	NPC70862
0.8294	Intermediate Similarity	NPC477991
0.8293	Intermediate Similarity	NPC284495
0.8293	Intermediate Similarity	NPC186325
0.8293	Intermediate Similarity	NPC312993
0.8289	Intermediate Similarity	NPC155211
0.8284	Intermediate Similarity	NPC473113
0.828	Intermediate Similarity	NPC12402
0.8278	Intermediate Similarity	NPC472262
0.8278	Intermediate Similarity	NPC288089
0.8278	Intermediate Similarity	NPC287604
0.8278	Intermediate Similarity	NPC161964
0.8272	Intermediate Similarity	NPC471456
0.8272	Intermediate Similarity	NPC3898
0.8258	Intermediate Similarity	NPC246638
0.8256	Intermediate Similarity	NPC473785
0.8253	Intermediate Similarity	NPC476505
0.8247	Intermediate Similarity	NPC242994
0.8247	Intermediate Similarity	NPC138099
0.8242	Intermediate Similarity	NPC137232
0.8242	Intermediate Similarity	NPC18380
0.8239	Intermediate Similarity	NPC2569
0.8239	Intermediate Similarity	NPC172329
0.8235	Intermediate Similarity	NPC472054
0.8232	Intermediate Similarity	NPC55443
0.8232	Intermediate Similarity	NPC177650
0.8232	Intermediate Similarity	NPC18699
0.8228	Intermediate Similarity	NPC143685
0.8217	Intermediate Similarity	NPC79627
0.8217	Intermediate Similarity	NPC10764
0.8214	Intermediate Similarity	NPC286230
0.8214	Intermediate Similarity	NPC253730
0.8212	Intermediate Similarity	NPC472591
0.8212	Intermediate Similarity	NPC52407
0.8212	Intermediate Similarity	NPC43627
0.8212	Intermediate Similarity	NPC53896
0.8212	Intermediate Similarity	NPC115458
0.821	Intermediate Similarity	NPC208806
0.821	Intermediate Similarity	NPC214632
0.821	Intermediate Similarity	NPC477691
0.8205	Intermediate Similarity	NPC469520
0.8204	Intermediate Similarity	NPC469664
0.8204	Intermediate Similarity	NPC169471
0.8198	Intermediate Similarity	NPC207467
0.8194	Intermediate Similarity	NPC275903
0.8193	Intermediate Similarity	NPC15374
0.8187	Intermediate Similarity	NPC329933
0.8187	Intermediate Similarity	NPC474310
0.8182	Intermediate Similarity	NPC292863
0.8182	Intermediate Similarity	NPC184326
0.8182	Intermediate Similarity	NPC185617
0.8176	Intermediate Similarity	NPC126767
0.8176	Intermediate Similarity	NPC56433
0.8176	Intermediate Similarity	NPC312929
0.8176	Intermediate Similarity	NPC245584
0.8176	Intermediate Similarity	NPC10842
0.8176	Intermediate Similarity	NPC289042
0.8176	Intermediate Similarity	NPC478002
0.8176	Intermediate Similarity	NPC118027
0.8176	Intermediate Similarity	NPC190648
0.8176	Intermediate Similarity	NPC183441
0.8171	Intermediate Similarity	NPC208258
0.8171	Intermediate Similarity	NPC474637
0.8171	Intermediate Similarity	NPC206641
0.8171	Intermediate Similarity	NPC208651
0.817	Intermediate Similarity	NPC472308
0.817	Intermediate Similarity	NPC272268
0.8161	Intermediate Similarity	NPC475662
0.8161	Intermediate Similarity	NPC473717
0.8161	Intermediate Similarity	NPC293227
0.8161	Intermediate Similarity	NPC473631
0.816	Intermediate Similarity	NPC174599
0.816	Intermediate Similarity	NPC79375
0.816	Intermediate Similarity	NPC82190
0.816	Intermediate Similarity	NPC37253
0.816	Intermediate Similarity	NPC472807
0.816	Intermediate Similarity	NPC192219
0.8158	Intermediate Similarity	NPC474097
0.8158	Intermediate Similarity	NPC50924
0.8155	Intermediate Similarity	NPC251336
0.8153	Intermediate Similarity	NPC476473
0.815	Intermediate Similarity	NPC72783
0.8148	Intermediate Similarity	NPC477690
0.8148	Intermediate Similarity	NPC154683
0.8148	Intermediate Similarity	NPC164912
0.8148	Intermediate Similarity	NPC40356
0.8144	Intermediate Similarity	NPC473009
0.8137	Intermediate Similarity	NPC294646
0.8137	Intermediate Similarity	NPC255641
0.8137	Intermediate Similarity	NPC290954
0.8137	Intermediate Similarity	NPC147735
0.8137	Intermediate Similarity	NPC470568
0.8133	Intermediate Similarity	NPC312273
0.8133	Intermediate Similarity	NPC301256
0.8129	Intermediate Similarity	NPC19622
0.8129	Intermediate Similarity	NPC65118
0.8129	Intermediate Similarity	NPC112789
0.8125	Intermediate Similarity	NPC106524
0.8125	Intermediate Similarity	NPC290695
0.8125	Intermediate Similarity	NPC94781

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 NPC317580 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
0.8452	Intermediate Similarity	NPD7390	Discontinued
0.8355	Intermediate Similarity	NPD5404	Approved
0.8355	Intermediate Similarity	NPD5406	Approved
0.8355	Intermediate Similarity	NPD5408	Approved
0.8355	Intermediate Similarity	NPD5405	Approved
0.8302	Intermediate Similarity	NPD3226	Approved
0.8263	Intermediate Similarity	NPD7473	Discontinued
0.8204	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6232	Discontinued
0.8141	Intermediate Similarity	NPD7003	Approved
0.8133	Intermediate Similarity	NPD6959	Discontinued
0.8052	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD8312	Approved
0.8035	Intermediate Similarity	NPD8313	Approved
0.8023	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD8150	Discontinued
0.7988	Intermediate Similarity	NPD7819	Suspended
0.7975	Intermediate Similarity	NPD7411	Suspended
0.7949	Intermediate Similarity	NPD2346	Discontinued
0.7939	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7458	Discontinued
0.7826	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7768	Phase 2
0.7744	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3749	Approved
0.7736	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD2532	Approved
0.7716	Intermediate Similarity	NPD2534	Approved
0.7716	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD2533	Approved
0.7707	Intermediate Similarity	NPD2799	Discontinued
0.7688	Intermediate Similarity	NPD8166	Discontinued
0.7682	Intermediate Similarity	NPD1470	Approved
0.7662	Intermediate Similarity	NPD3764	Approved
0.7647	Intermediate Similarity	NPD8320	Phase 1
0.7647	Intermediate Similarity	NPD8319	Approved
0.7562	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7871	Phase 2
0.7553	Intermediate Similarity	NPD7870	Phase 2
0.7543	Intermediate Similarity	NPD5844	Phase 1
0.7541	Intermediate Similarity	NPD6535	Approved
0.7541	Intermediate Similarity	NPD6534	Approved
0.7514	Intermediate Similarity	NPD7699	Phase 2
0.7514	Intermediate Similarity	NPD7700	Phase 2
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7435	Discontinued
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7485	Intermediate Similarity	NPD4380	Phase 2
0.7436	Intermediate Similarity	NPD2313	Discontinued
0.7433	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD6780	Approved
0.7433	Intermediate Similarity	NPD6781	Approved
0.7433	Intermediate Similarity	NPD6776	Approved
0.7433	Intermediate Similarity	NPD6782	Approved
0.7433	Intermediate Similarity	NPD6777	Approved
0.7433	Intermediate Similarity	NPD6778	Approved
0.7427	Intermediate Similarity	NPD7075	Discontinued
0.7417	Intermediate Similarity	NPD1201	Approved
0.7407	Intermediate Similarity	NPD7696	Phase 3
0.7407	Intermediate Similarity	NPD7697	Approved
0.7407	Intermediate Similarity	NPD7698	Approved
0.7391	Intermediate Similarity	NPD6212	Phase 3
0.7391	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2344	Approved
0.7391	Intermediate Similarity	NPD6213	Phase 3
0.7368	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3750	Approved
0.736	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1607	Approved
0.7358	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7874	Approved
0.7353	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6273	Approved
0.7338	Intermediate Similarity	NPD1164	Approved
0.7325	Intermediate Similarity	NPD3268	Approved
0.7288	Intermediate Similarity	NPD7177	Discontinued
0.7273	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6166	Phase 2
0.7267	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1510	Phase 2
0.7254	Intermediate Similarity	NPD7701	Phase 2
0.7251	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD9493	Approved
0.7233	Intermediate Similarity	NPD1240	Approved
0.7231	Intermediate Similarity	NPD7801	Approved
0.7222	Intermediate Similarity	NPD6559	Discontinued
0.7212	Intermediate Similarity	NPD2309	Approved
0.7209	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD8285	Discontinued
0.7193	Intermediate Similarity	NPD6801	Discontinued
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2798	Approved
0.7178	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1471	Phase 3
0.7176	Intermediate Similarity	NPD6599	Discontinued
0.7164	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4308	Phase 3
0.7159	Intermediate Similarity	NPD5710	Approved
0.7159	Intermediate Similarity	NPD5711	Approved
0.7158	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7008	Discontinued
0.7151	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2801	Approved
0.715	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5494	Approved
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1549	Phase 2
0.7133	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD943	Approved
0.7125	Intermediate Similarity	NPD2979	Phase 3
0.712	Intermediate Similarity	NPD8434	Phase 2
0.7115	Intermediate Similarity	NPD1203	Approved
0.711	Intermediate Similarity	NPD3817	Phase 2
0.7095	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1934	Approved
0.7089	Intermediate Similarity	NPD6832	Phase 2
0.7083	Intermediate Similarity	NPD6823	Phase 2
0.7078	Intermediate Similarity	NPD1281	Approved
0.7073	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5953	Discontinued
0.7066	Intermediate Similarity	NPD3300	Phase 2
0.7066	Intermediate Similarity	NPD7236	Approved
0.7059	Intermediate Similarity	NPD7239	Suspended
0.7059	Intermediate Similarity	NPD4626	Approved
0.7055	Intermediate Similarity	NPD3748	Approved
0.7052	Intermediate Similarity	NPD1465	Phase 2
0.7048	Intermediate Similarity	NPD4628	Phase 3
0.7048	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6799	Approved
0.7024	Intermediate Similarity	NPD1511	Approved
0.7017	Intermediate Similarity	NPD7074	Phase 3
0.7012	Intermediate Similarity	NPD2438	Suspended
0.7012	Intermediate Similarity	NPD2796	Approved
0.7012	Intermediate Similarity	NPD1551	Phase 2
0.7011	Intermediate Similarity	NPD5402	Approved
0.7006	Intermediate Similarity	NPD3266	Approved
0.7006	Intermediate Similarity	NPD2797	Approved
0.7006	Intermediate Similarity	NPD3267	Approved
0.7006	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD3818	Discontinued
0.7	Intermediate Similarity	NPD411	Approved
0.6975	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD230	Phase 1
0.6975	Remote Similarity	NPD447	Suspended
0.6971	Remote Similarity	NPD3882	Suspended
0.6966	Remote Similarity	NPD7229	Phase 3
0.6961	Remote Similarity	NPD7054	Approved
0.6957	Remote Similarity	NPD6663	Approved
0.6954	Remote Similarity	NPD8455	Phase 2
0.6951	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3019	Approved
0.6946	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1512	Approved
0.6939	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD9545	Approved
0.6923	Remote Similarity	NPD3972	Approved
0.6923	Remote Similarity	NPD7472	Approved
0.6923	Remote Similarity	NPD9717	Approved
0.6918	Remote Similarity	NPD5736	Approved
0.6914	Remote Similarity	NPD4307	Phase 2
0.6914	Remote Similarity	NPD4060	Phase 1
0.6909	Remote Similarity	NPD6100	Approved
0.6909	Remote Similarity	NPD6099	Approved
0.6906	Remote Similarity	NPD3751	Discontinued
0.6902	Remote Similarity	NPD7808	Phase 3
0.6902	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD920	Approved
0.6897	Remote Similarity	NPD37	Approved
0.6893	Remote Similarity	NPD6234	Discontinued
0.689	Remote Similarity	NPD7097	Phase 1
0.6887	Remote Similarity	NPD5951	Approved
0.6886	Remote Similarity	NPD2800	Approved
0.6885	Remote Similarity	NPD6797	Phase 2
0.6883	Remote Similarity	NPD1651	Approved
0.6883	Remote Similarity	NPD5691	Approved
0.6879	Remote Similarity	NPD6585	Discontinued
0.6875	Remote Similarity	NPD4967	Phase 2
0.6875	Remote Similarity	NPD4966	Approved
0.6875	Remote Similarity	NPD4965	Approved
0.6872	Remote Similarity	NPD6808	Phase 2
0.6868	Remote Similarity	NPD7286	Phase 2
0.6862	Remote Similarity	NPD4287	Approved
0.6852	Remote Similarity	NPD8032	Phase 2
0.6848	Remote Similarity	NPD7251	Discontinued
0.6839	Remote Similarity	NPD2932	Approved
0.6839	Remote Similarity	NPD5890	Approved
0.6839	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5889	Approved
0.6835	Remote Similarity	NPD1876	Approved
0.6833	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6651	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