NPASS Compound

Structure

CID318270 OpenBabel06191716142D 46 51 0 0 1 0 0 0 0 0999 V2000 7.3148 2.9933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6492 4.1265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7946 -0.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8473 -0.4743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0764 0.1512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5687 2.0459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4881 -0.0346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1290 0.4051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5934 0.4731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7699 0.8447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 -1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8752 1.3524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5160 1.7921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2343 0.9128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4355 -0.2884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2870 1.1666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9278 1.6063 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 9.2095 2.4856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 0.9808 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6987 0.9808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7172 0.5909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3975 -1.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6893 -1.2358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0331 2.1139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6740 2.5536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -0.4904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1569 2.2318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 -3.4327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5707 1.9531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9557 3.4329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -3.4327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 45 1 0 0 0 0 4 46 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 16 1 0 0 0 0 7 19 2 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 17 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 12 22 2 0 0 0 0 12 24 1 0 0 0 0 13 23 2 0 0 0 0 13 25 1 0 0 0 0 14 26 2 0 0 0 0 14 28 1 0 0 0 0 15 22 1 0 0 0 0 15 28 1 0 0 0 0 16 27 2 0 0 0 0 16 34 1 0 0 0 0 17 29 2 0 0 0 0 17 34 1 0 0 0 0 18 23 1 0 0 0 0 18 34 1 0 0 0 0 19 27 1 0 0 0 0 19 35 1 0 0 0 0 20 24 2 0 0 0 0 20 36 1 0 0 0 0 21 25 2 0 0 0 0 21 37 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 28 38 2 0 0 0 0 29 39 1 0 0 0 0 30 40 2 0 0 0 0 31 41 2 0 0 0 0 32 42 2 0 0 0 0 32 45 1 0 0 0 0 33 43 2 0 0 0 0 33 46 1 0 0 0 0 34 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.13
Volume:	605.944
LogP:	5.379
LogD:	2.113
LogS:	-5.891
# Rotatable Bonds:	5
TPSA:	204.96
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.183
Synthetic Accessibility Score:	3.858
Fsp3:	0.147
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:	-6.175
MDCK Permeability:	8.225874807976652e-06
Pgp-inhibitor:	0.837
Pgp-substrate:	0.195
Human Intestinal Absorption (HIA):	0.916
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	100.18760681152344%
Volume Distribution (VD):	0.166
Pgp-substrate:	1.6909512281417847%

ADMET: Metabolism

CYP1A2-inhibitor:	0.31
CYP1A2-substrate:	0.737
CYP2C19-inhibitor:	0.258
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.728
CYP2C9-substrate:	0.187
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.249
CYP3A4-substrate:	0.303

ADMET: Excretion

Clearance (CL):	0.531
Half-life (T1/2):	0.025

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.449
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.155
Carcinogencity:	0.173
Eye Corrosion:	0.003
Eye Irritation:	0.904
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC318270

Natural Product ID:	NPC318270
*Common Name:**	Scutianthraquinone C
IUPAC Name:	methyl 3,8-dihydroxy-1-methyl-9,10-dioxo-7-(2,5,9-trihydroxy-3-methoxycarbonyl-4-methyl-10-oxoanthracen-9-yl)anthracene-2-carboxylate
Synonyms:	Scutianthraquinone C
Standard InCHIKey:	JFUFATWECSQGDK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C34H24O12/c1-12-22-15(10-20(36)24(12)32(42)45-3)28(38)14-8-9-17(29(39)26(14)30(22)40)34(44)16-6-5-7-19(35)27(16)31(41)23-13(2)25(33(43)46-4)21(37)11-18(23)34/h5-11,35-37,39,44H,1-4H3
SMILES:	COC(=O)c1c(O)cc2c(c1C)C(=O)c1c(C2(O)c2ccc3c(c2O)C(=O)c2c(C3=O)cc(c(c2C)C(=O)OC)O)cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451608
PubChem CID:	44592159
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	>	16000.0	nM	PMID[459742]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3140.0	nM	PMID[459742]
NPT2	Others	Unspecified		Ratio IC50	>	5.0	n.a.	PMID[459742]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	15400.0	nM	PMID[459742]
NPT2	Others	Unspecified		Ratio IC50	>	1.0	n.a.	PMID[459742]

☑ 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 NPC318270 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	366
0.1-0.2	1630
0.2-0.3	3508
0.3-0.4	8555
0.4-0.5	10305
0.5-0.6	4795
0.6-0.7	6906
0.7-0.8	6173
0.8-0.85	388
0.85-0.9	63
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9866	High Similarity	NPC317580
0.98	High Similarity	NPC326084
0.9735	High Similarity	NPC475449
0.9252	High Similarity	NPC66593
0.9091	High Similarity	NPC66029
0.9079	High Similarity	NPC205766
0.9067	High Similarity	NPC314437
0.8993	High Similarity	NPC471682
0.8954	High Similarity	NPC315520
0.894	High Similarity	NPC147250
0.8926	High Similarity	NPC257644
0.8912	High Similarity	NPC4214
0.8882	High Similarity	NPC119767
0.8874	High Similarity	NPC471683
0.8861	High Similarity	NPC472060
0.8861	High Similarity	NPC472052
0.8861	High Similarity	NPC470342
0.88	High Similarity	NPC19631
0.88	High Similarity	NPC239136
0.879	High Similarity	NPC474861
0.8758	High Similarity	NPC37709
0.8742	High Similarity	NPC53016
0.8742	High Similarity	NPC296752
0.872	High Similarity	NPC477836
0.8707	High Similarity	NPC80035
0.8704	High Similarity	NPC477835
0.8667	High Similarity	NPC225243
0.8667	High Similarity	NPC315578
0.8662	High Similarity	NPC218870
0.8662	High Similarity	NPC474622
0.8662	High Similarity	NPC474621
0.8662	High Similarity	NPC182921
0.8662	High Similarity	NPC470408
0.8662	High Similarity	NPC474824
0.8658	High Similarity	NPC13715
0.8636	High Similarity	NPC478018
0.8627	High Similarity	NPC478019
0.8625	High Similarity	NPC476506
0.8616	High Similarity	NPC263483
0.8608	High Similarity	NPC226656
0.8608	High Similarity	NPC66508
0.86	High Similarity	NPC26924
0.8562	High Similarity	NPC193703
0.8562	High Similarity	NPC227841
0.8562	High Similarity	NPC21599
0.8562	High Similarity	NPC324736
0.8553	High Similarity	NPC69755
0.8537	High Similarity	NPC76647
0.8526	High Similarity	NPC477221
0.8519	High Similarity	NPC315772
0.8516	High Similarity	NPC290194
0.8506	High Similarity	NPC34482
0.8497	Intermediate Similarity	NPC174905
0.8497	Intermediate Similarity	NPC295712
0.8497	Intermediate Similarity	NPC451542
0.8497	Intermediate Similarity	NPC474203
0.8497	Intermediate Similarity	NPC313047
0.8497	Intermediate Similarity	NPC293545
0.8487	Intermediate Similarity	NPC290550
0.8481	Intermediate Similarity	NPC474533
0.8481	Intermediate Similarity	NPC474534
0.8467	Intermediate Similarity	NPC62272
0.8457	Intermediate Similarity	NPC472261
0.8452	Intermediate Similarity	NPC271944
0.8452	Intermediate Similarity	NPC110882
0.8452	Intermediate Similarity	NPC470570
0.8452	Intermediate Similarity	NPC85393
0.8446	Intermediate Similarity	NPC225051
0.8442	Intermediate Similarity	NPC48762
0.8438	Intermediate Similarity	NPC474360
0.8434	Intermediate Similarity	NPC478021
0.8431	Intermediate Similarity	NPC193555
0.8424	Intermediate Similarity	NPC470341
0.8424	Intermediate Similarity	NPC105414
0.8424	Intermediate Similarity	NPC324522
0.8424	Intermediate Similarity	NPC234497
0.8424	Intermediate Similarity	NPC472058
0.8421	Intermediate Similarity	NPC168471
0.8415	Intermediate Similarity	NPC71390
0.8415	Intermediate Similarity	NPC478022
0.8415	Intermediate Similarity	NPC478020
0.84	Intermediate Similarity	NPC155211
0.8395	Intermediate Similarity	NPC284495
0.8393	Intermediate Similarity	NPC477991
0.8393	Intermediate Similarity	NPC477992
0.8389	Intermediate Similarity	NPC288089
0.8387	Intermediate Similarity	NPC12402
0.8385	Intermediate Similarity	NPC67197
0.8383	Intermediate Similarity	NPC294501
0.8383	Intermediate Similarity	NPC473113
0.8375	Intermediate Similarity	NPC266469
0.8373	Intermediate Similarity	NPC175477
0.8366	Intermediate Similarity	NPC246638
0.8364	Intermediate Similarity	NPC30027
0.8355	Intermediate Similarity	NPC138099
0.8355	Intermediate Similarity	NPC242994
0.8354	Intermediate Similarity	NPC477914
0.8354	Intermediate Similarity	NPC476505
0.8344	Intermediate Similarity	NPC172329
0.8344	Intermediate Similarity	NPC273467
0.8344	Intermediate Similarity	NPC2569
0.8344	Intermediate Similarity	NPC189552
0.8323	Intermediate Similarity	NPC79627
0.8323	Intermediate Similarity	NPC10764
0.8323	Intermediate Similarity	NPC146211
0.8323	Intermediate Similarity	NPC478027
0.8322	Intermediate Similarity	NPC52407
0.8322	Intermediate Similarity	NPC53896
0.8313	Intermediate Similarity	NPC208806
0.8313	Intermediate Similarity	NPC107009
0.8312	Intermediate Similarity	NPC85310
0.8302	Intermediate Similarity	NPC477276
0.8301	Intermediate Similarity	NPC169452
0.8301	Intermediate Similarity	NPC181560
0.8293	Intermediate Similarity	NPC97637
0.8293	Intermediate Similarity	NPC187934
0.8284	Intermediate Similarity	NPC70862
0.8282	Intermediate Similarity	NPC312993
0.8282	Intermediate Similarity	NPC186325
0.828	Intermediate Similarity	NPC312929
0.828	Intermediate Similarity	NPC126767
0.828	Intermediate Similarity	NPC190648
0.828	Intermediate Similarity	NPC118027
0.828	Intermediate Similarity	NPC289042
0.828	Intermediate Similarity	NPC56433
0.828	Intermediate Similarity	NPC245584
0.8267	Intermediate Similarity	NPC50924
0.8267	Intermediate Similarity	NPC287604
0.8267	Intermediate Similarity	NPC161964
0.8267	Intermediate Similarity	NPC472262
0.8261	Intermediate Similarity	NPC3898
0.825	Intermediate Similarity	NPC164912
0.8239	Intermediate Similarity	NPC470568
0.8239	Intermediate Similarity	NPC290954
0.8239	Intermediate Similarity	NPC147735
0.8239	Intermediate Similarity	NPC255641
0.8239	Intermediate Similarity	NPC294646
0.8231	Intermediate Similarity	NPC95537
0.8228	Intermediate Similarity	NPC471907
0.8225	Intermediate Similarity	NPC472054
0.8224	Intermediate Similarity	NPC245923
0.8224	Intermediate Similarity	NPC53206
0.8224	Intermediate Similarity	NPC53414
0.8224	Intermediate Similarity	NPC471905
0.8221	Intermediate Similarity	NPC55443
0.8221	Intermediate Similarity	NPC177650
0.8221	Intermediate Similarity	NPC18699
0.8217	Intermediate Similarity	NPC143685
0.8217	Intermediate Similarity	NPC225173
0.8217	Intermediate Similarity	NPC163846
0.8217	Intermediate Similarity	NPC300540
0.8212	Intermediate Similarity	NPC283088
0.821	Intermediate Similarity	NPC279605
0.82	Intermediate Similarity	NPC43627
0.82	Intermediate Similarity	NPC115458
0.8199	Intermediate Similarity	NPC214632
0.8199	Intermediate Similarity	NPC477691
0.8194	Intermediate Similarity	NPC135524
0.8194	Intermediate Similarity	NPC469520
0.8194	Intermediate Similarity	NPC73061
0.8193	Intermediate Similarity	NPC469664
0.8188	Intermediate Similarity	NPC93015
0.8187	Intermediate Similarity	NPC207467
0.8187	Intermediate Similarity	NPC35
0.8187	Intermediate Similarity	NPC470569
0.8187	Intermediate Similarity	NPC118427
0.8187	Intermediate Similarity	NPC478000
0.8182	Intermediate Similarity	NPC96421
0.8182	Intermediate Similarity	NPC275903
0.8176	Intermediate Similarity	NPC329933
0.8171	Intermediate Similarity	NPC185617
0.8166	Intermediate Similarity	NPC183441
0.8165	Intermediate Similarity	NPC10842
0.8165	Intermediate Similarity	NPC125801
0.8165	Intermediate Similarity	NPC34802
0.816	Intermediate Similarity	NPC474637
0.816	Intermediate Similarity	NPC208651
0.816	Intermediate Similarity	NPC206641
0.8158	Intermediate Similarity	NPC272268
0.8158	Intermediate Similarity	NPC472308
0.8158	Intermediate Similarity	NPC254847
0.8158	Intermediate Similarity	NPC118919
0.8158	Intermediate Similarity	NPC474813
0.8148	Intermediate Similarity	NPC471456
0.8146	Intermediate Similarity	NPC474097
0.8141	Intermediate Similarity	NPC476473
0.8141	Intermediate Similarity	NPC163948
0.814	Intermediate Similarity	NPC72783
0.814	Intermediate Similarity	NPC473785
0.8137	Intermediate Similarity	NPC40356
0.8137	Intermediate Similarity	NPC477690
0.8137	Intermediate Similarity	NPC154683
0.8129	Intermediate Similarity	NPC204045
0.8129	Intermediate Similarity	NPC305845
0.8129	Intermediate Similarity	NPC124365
0.8125	Intermediate Similarity	NPC280295
0.8121	Intermediate Similarity	NPC18380
0.8121	Intermediate Similarity	NPC31799
0.8121	Intermediate Similarity	NPC199253
0.8121	Intermediate Similarity	NPC136588

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 NPC318270 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	995
0.2-0.3	1476
0.3-0.4	2604
0.4-0.5	2130
0.5-0.6	1107
0.6-0.7	355
0.7-0.8	141
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
0.8562	High Similarity	NPD7390	Discontinued
0.8467	Intermediate Similarity	NPD5404	Approved
0.8467	Intermediate Similarity	NPD5405	Approved
0.8467	Intermediate Similarity	NPD5406	Approved
0.8467	Intermediate Similarity	NPD5408	Approved
0.8293	Intermediate Similarity	NPD6232	Discontinued
0.8291	Intermediate Similarity	NPD3226	Approved
0.8253	Intermediate Similarity	NPD7473	Discontinued
0.8193	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7003	Approved
0.8121	Intermediate Similarity	NPD6959	Discontinued
0.8105	Intermediate Similarity	NPD2935	Discontinued
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7819	Suspended
0.7963	Intermediate Similarity	NPD7411	Suspended
0.7935	Intermediate Similarity	NPD2346	Discontinued
0.7919	Intermediate Similarity	NPD8312	Approved
0.7919	Intermediate Similarity	NPD8313	Approved
0.7886	Intermediate Similarity	NPD8150	Discontinued
0.784	Intermediate Similarity	NPD7458	Discontinued
0.7818	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1470	Approved
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7725	Intermediate Similarity	NPD3749	Approved
0.7722	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2533	Approved
0.7702	Intermediate Similarity	NPD2534	Approved
0.7702	Intermediate Similarity	NPD2532	Approved
0.7647	Intermediate Similarity	NPD3764	Approved
0.7622	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2799	Discontinued
0.7562	Intermediate Similarity	NPD8166	Discontinued
0.754	Intermediate Similarity	NPD8320	Phase 1
0.754	Intermediate Similarity	NPD8319	Approved
0.754	Intermediate Similarity	NPD7870	Phase 2
0.754	Intermediate Similarity	NPD7871	Phase 2
0.7529	Intermediate Similarity	NPD5844	Phase 1
0.7527	Intermediate Similarity	NPD6534	Approved
0.7527	Intermediate Similarity	NPD6535	Approved
0.7517	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD7699	Phase 2
0.75	Intermediate Similarity	NPD7700	Phase 2
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7485	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8151	Discontinued
0.747	Intermediate Similarity	NPD4380	Phase 2
0.7452	Intermediate Similarity	NPD1607	Approved
0.7438	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1164	Approved
0.7419	Intermediate Similarity	NPD6782	Approved
0.7419	Intermediate Similarity	NPD6778	Approved
0.7419	Intermediate Similarity	NPD6776	Approved
0.7419	Intermediate Similarity	NPD6777	Approved
0.7419	Intermediate Similarity	NPD2313	Discontinued
0.7419	Intermediate Similarity	NPD6779	Approved
0.7419	Intermediate Similarity	NPD6780	Approved
0.7419	Intermediate Similarity	NPD6781	Approved
0.7412	Intermediate Similarity	NPD7075	Discontinued
0.7394	Intermediate Similarity	NPD7698	Approved
0.7394	Intermediate Similarity	NPD7696	Phase 3
0.7394	Intermediate Similarity	NPD7697	Approved
0.7377	Intermediate Similarity	NPD6212	Phase 3
0.7377	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6213	Phase 3
0.7375	Intermediate Similarity	NPD2344	Approved
0.7358	Intermediate Similarity	NPD1510	Phase 2
0.7353	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD9493	Approved
0.7346	Intermediate Similarity	NPD3750	Approved
0.7345	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7874	Approved
0.7344	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1240	Approved
0.7273	Intermediate Similarity	NPD7177	Discontinued
0.7257	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6166	Phase 2
0.7255	Intermediate Similarity	NPD1283	Approved
0.725	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7008	Discontinued
0.724	Intermediate Similarity	NPD7701	Phase 2
0.7235	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6273	Approved
0.7215	Intermediate Similarity	NPD943	Approved
0.7207	Intermediate Similarity	NPD6559	Discontinued
0.7197	Intermediate Similarity	NPD3268	Approved
0.7195	Intermediate Similarity	NPD2309	Approved
0.7193	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8285	Discontinued
0.7176	Intermediate Similarity	NPD6801	Discontinued
0.7161	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD6599	Discontinued
0.716	Intermediate Similarity	NPD1471	Phase 3
0.7152	Intermediate Similarity	NPD4626	Approved
0.715	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD5710	Approved
0.7135	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2801	Approved
0.7135	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7801	Approved
0.7128	Intermediate Similarity	NPD7783	Phase 2
0.7117	Intermediate Similarity	NPD1549	Phase 2
0.711	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1203	Approved
0.7093	Intermediate Similarity	NPD3817	Phase 2
0.7079	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1934	Approved
0.707	Intermediate Similarity	NPD6832	Phase 2
0.7068	Intermediate Similarity	NPD6823	Phase 2
0.7066	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1281	Approved
0.7056	Intermediate Similarity	NPD5953	Discontinued
0.7055	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3300	Phase 2
0.7037	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3748	Approved
0.7035	Intermediate Similarity	NPD1465	Phase 2
0.703	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4628	Phase 3
0.7029	Intermediate Similarity	NPD5494	Approved
0.7025	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3972	Approved
0.7011	Intermediate Similarity	NPD8434	Phase 2
0.7006	Intermediate Similarity	NPD1511	Approved
0.7006	Intermediate Similarity	NPD6799	Approved
0.7	Intermediate Similarity	NPD7074	Phase 3
0.7	Intermediate Similarity	NPD2979	Phase 3
0.6994	Remote Similarity	NPD2796	Approved
0.6994	Remote Similarity	NPD1551	Phase 2
0.6994	Remote Similarity	NPD5402	Approved
0.6988	Remote Similarity	NPD6190	Approved
0.6983	Remote Similarity	NPD3818	Discontinued
0.6982	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD411	Approved
0.698	Remote Similarity	NPD5951	Approved
0.6974	Remote Similarity	NPD1651	Approved
0.6957	Remote Similarity	NPD447	Suspended
0.6957	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD230	Phase 1
0.6954	Remote Similarity	NPD3882	Suspended
0.6946	Remote Similarity	NPD7236	Approved
0.6944	Remote Similarity	NPD7054	Approved
0.6941	Remote Similarity	NPD7239	Suspended
0.6936	Remote Similarity	NPD8455	Phase 2
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3019	Approved
0.6928	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1512	Approved
0.6908	Remote Similarity	NPD9545	Approved
0.6906	Remote Similarity	NPD7472	Approved
0.6903	Remote Similarity	NPD9717	Approved
0.6894	Remote Similarity	NPD4307	Phase 2
0.689	Remote Similarity	NPD2438	Suspended
0.6889	Remote Similarity	NPD3751	Discontinued
0.6885	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7808	Phase 3
0.6882	Remote Similarity	NPD920	Approved
0.6879	Remote Similarity	NPD2797	Approved
0.6879	Remote Similarity	NPD37	Approved
0.6879	Remote Similarity	NPD3266	Approved
0.6879	Remote Similarity	NPD3267	Approved
0.6868	Remote Similarity	NPD6797	Phase 2
0.6867	Remote Similarity	NPD2800	Approved
0.6863	Remote Similarity	NPD5691	Approved
0.6863	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6585	Discontinued
0.6854	Remote Similarity	NPD7229	Phase 3
0.6854	Remote Similarity	NPD6808	Phase 2
0.6851	Remote Similarity	NPD7286	Phase 2
0.6845	Remote Similarity	NPD4287	Approved
0.6832	Remote Similarity	NPD6663	Approved
0.6831	Remote Similarity	NPD7251	Discontinued
0.6821	Remote Similarity	NPD5890	Approved
0.6821	Remote Similarity	NPD5889	Approved
0.6818	Remote Similarity	NPD2932	Approved
0.6816	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1876	Approved
0.681	Remote Similarity	NPD6651	Approved
0.6805	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD74	Approved
0.6803	Remote Similarity	NPD9266	Approved
0.6792	Remote Similarity	NPD5736	Approved
0.679	Remote Similarity	NPD4060	Phase 1
0.6788	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6099	Approved
0.6788	Remote Similarity	NPD6100	Approved
0.6784	Remote Similarity	NPD5403	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