NPASS Compound

Structure

CID308943 OpenBabel06191716112D 24 27 0 0 0 0 0 0 0 0999 V2000 0.0053 0.9665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0148 -4.8350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3599 -4.3427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1860 -0.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1903 -1.4421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3521 -0.0051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3606 -1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6842 0.0099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0065 -2.9044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5225 -0.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5267 -1.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0015 -1.9312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8441 -0.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8411 -3.3854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8366 -1.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6867 -1.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8360 -1.4452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 -2.9033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 -0.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6735 -1.9269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 0.0054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8464 -4.3487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5087 -3.3899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 8 10 1 0 0 0 0 8 13 2 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	321.1
Volume:	325.384
LogP:	3.317
LogD:	2.789
LogS:	-6.622
# Rotatable Bonds:	2
TPSA:	55.84
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.537
Synthetic Accessibility Score:	2.508
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.713
MDCK Permeability:	5.192948810872622e-05
Pgp-inhibitor:	0.563
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.221
Plasma Protein Binding (PPB):	87.79637145996094%
Volume Distribution (VD):	0.625
Pgp-substrate:	10.453598976135254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.936
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.764
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.732
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.459
CYP2D6-substrate:	0.569
CYP3A4-inhibitor:	0.593
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	1.883
Half-life (T1/2):	0.244

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.809
Rat Oral Acute Toxicity:	0.172
Maximum Recommended Daily Dose:	0.534
Skin Sensitization:	0.659
Carcinogencity:	0.714
Eye Corrosion:	0.006
Eye Irritation:	0.587
Respiratory Toxicity:	0.285

Download Data

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

Natural Product: NPC308943

Natural Product ID:	NPC308943
*Common Name:**	Cepharadione B
IUPAC Name:	n.a.
Synonyms:	cepharadione B
Standard InCHIKey:	AFKGBLKLNRDQFN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H15NO4/c1-20-13-8-10-6-4-5-7-11(10)16-15(13)12(17(21)19(20)22)9-14(23-2)18(16)24-3/h4-9H,1-3H3
SMILES:	CN1c2cc3ccccc3c3c2c(cc(c3OC)OC)C(=O)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL396085
PubChem CID:	189151
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines [CHEMONTID:0003326] 4,5-dioxoaporphines

*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
NPO5928	Streptomyces nashvillensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1490884]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29099182]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868158]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11088	Ganoderma capense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11088	Ganoderma capense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO868	Cephalaria gigantea	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9030	Couroupita guianensis	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5928	Streptomyces nashvillensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2400	Streptomyces mediolani	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11715	Polygonum aubertii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3584	Oyedaea buphthalmoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12667	Goniodoma pseudogoniaulax	Species	Coleophoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11088	Ganoderma capense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11010	Melampyrum elatius	Species	Orobanchaceae	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
GI50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[541689]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[541689]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	22.8	ug.mL-1	PMID[541689]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[541689]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[541689]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	36.1	ug.mL-1	PMID[541689]

☑ 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 NPC308943 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	473
0.1-0.2	2740
0.2-0.3	10528
0.3-0.4	6294
0.4-0.5	7867
0.5-0.6	12638
0.6-0.7	1952
0.7-0.8	185
0.8-0.85	13
0.85-0.9	1
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9632	High Similarity	NPC55470
0.9572	High Similarity	NPC222561
0.9227	High Similarity	NPC298449
0.9016	High Similarity	NPC100573
0.9016	High Similarity	NPC207873
0.8724	High Similarity	NPC90185
0.8698	High Similarity	NPC5374
0.8632	High Similarity	NPC254957
0.8549	High Similarity	NPC71124
0.852	High Similarity	NPC207971
0.8432	Intermediate Similarity	NPC285941
0.8384	Intermediate Similarity	NPC268077
0.8359	Intermediate Similarity	NPC17677
0.8359	Intermediate Similarity	NPC23080
0.8359	Intermediate Similarity	NPC193906
0.8298	Intermediate Similarity	NPC190461
0.8168	Intermediate Similarity	NPC249405
0.8141	Intermediate Similarity	NPC471489
0.8125	Intermediate Similarity	NPC33902
0.8125	Intermediate Similarity	NPC276674
0.8041	Intermediate Similarity	NPC320088
0.8	Intermediate Similarity	NPC312531
0.7927	Intermediate Similarity	NPC179704
0.7925	Intermediate Similarity	NPC210434
0.787	Intermediate Similarity	NPC24019
0.7865	Intermediate Similarity	NPC222524
0.7865	Intermediate Similarity	NPC287588
0.7843	Intermediate Similarity	NPC38961
0.7817	Intermediate Similarity	NPC474904
0.7763	Intermediate Similarity	NPC22481
0.77	Intermediate Similarity	NPC78284
0.7692	Intermediate Similarity	NPC85661
0.7667	Intermediate Similarity	NPC10732
0.7663	Intermediate Similarity	NPC119669
0.7658	Intermediate Similarity	NPC189903
0.7658	Intermediate Similarity	NPC182907
0.7647	Intermediate Similarity	NPC90875
0.7644	Intermediate Similarity	NPC46679
0.7636	Intermediate Similarity	NPC233334
0.7626	Intermediate Similarity	NPC278525
0.7619	Intermediate Similarity	NPC61731
0.7619	Intermediate Similarity	NPC153631
0.7619	Intermediate Similarity	NPC186569
0.7613	Intermediate Similarity	NPC108342
0.7612	Intermediate Similarity	NPC302001
0.7608	Intermediate Similarity	NPC171882
0.7608	Intermediate Similarity	NPC121510
0.759	Intermediate Similarity	NPC5167
0.7588	Intermediate Similarity	NPC169387
0.7588	Intermediate Similarity	NPC270515
0.7588	Intermediate Similarity	NPC477259
0.7576	Intermediate Similarity	NPC116007
0.7552	Intermediate Similarity	NPC471604
0.755	Intermediate Similarity	NPC208890
0.7547	Intermediate Similarity	NPC124658
0.7547	Intermediate Similarity	NPC227361
0.7537	Intermediate Similarity	NPC162653
0.7536	Intermediate Similarity	NPC220241
0.7536	Intermediate Similarity	NPC295479
0.7513	Intermediate Similarity	NPC241055
0.7512	Intermediate Similarity	NPC212163
0.7512	Intermediate Similarity	NPC146976
0.75	Intermediate Similarity	NPC91234
0.75	Intermediate Similarity	NPC85613
0.7489	Intermediate Similarity	NPC15406
0.7489	Intermediate Similarity	NPC476220
0.7489	Intermediate Similarity	NPC160113
0.7489	Intermediate Similarity	NPC253675
0.7489	Intermediate Similarity	NPC285254
0.7487	Intermediate Similarity	NPC83511
0.7473	Intermediate Similarity	NPC326316
0.7473	Intermediate Similarity	NPC81733
0.7467	Intermediate Similarity	NPC166722
0.7465	Intermediate Similarity	NPC236668
0.7456	Intermediate Similarity	NPC124313
0.7455	Intermediate Similarity	NPC154922
0.7454	Intermediate Similarity	NPC256422
0.7446	Intermediate Similarity	NPC137353
0.7445	Intermediate Similarity	NPC84164
0.7445	Intermediate Similarity	NPC207283
0.744	Intermediate Similarity	NPC295676
0.7435	Intermediate Similarity	NPC24954
0.743	Intermediate Similarity	NPC290227
0.7418	Intermediate Similarity	NPC159815
0.7409	Intermediate Similarity	NPC470018
0.7406	Intermediate Similarity	NPC470020
0.7401	Intermediate Similarity	NPC210296
0.7395	Intermediate Similarity	NPC240684
0.7383	Intermediate Similarity	NPC268223
0.7382	Intermediate Similarity	NPC135006
0.7368	Intermediate Similarity	NPC72905
0.7368	Intermediate Similarity	NPC476572
0.7368	Intermediate Similarity	NPC93653
0.7366	Intermediate Similarity	NPC477258
0.7358	Intermediate Similarity	NPC168409
0.7357	Intermediate Similarity	NPC304837
0.7357	Intermediate Similarity	NPC476258
0.7354	Intermediate Similarity	NPC325871
0.7354	Intermediate Similarity	NPC99659
0.7347	Intermediate Similarity	NPC303581
0.7347	Intermediate Similarity	NPC67978
0.7344	Intermediate Similarity	NPC299582
0.7337	Intermediate Similarity	NPC27887
0.7337	Intermediate Similarity	NPC220961
0.7336	Intermediate Similarity	NPC470481
0.7336	Intermediate Similarity	NPC470482
0.7333	Intermediate Similarity	NPC156728
0.7333	Intermediate Similarity	NPC244606
0.733	Intermediate Similarity	NPC24228
0.7327	Intermediate Similarity	NPC182853
0.7327	Intermediate Similarity	NPC195120
0.7324	Intermediate Similarity	NPC25961
0.7315	Intermediate Similarity	NPC38964
0.7306	Intermediate Similarity	NPC7560
0.7306	Intermediate Similarity	NPC476569
0.73	Intermediate Similarity	NPC298339
0.7296	Intermediate Similarity	NPC183537
0.7293	Intermediate Similarity	NPC113455
0.7286	Intermediate Similarity	NPC41216
0.7273	Intermediate Similarity	NPC308267
0.726	Intermediate Similarity	NPC318525
0.726	Intermediate Similarity	NPC207239
0.726	Intermediate Similarity	NPC10653
0.7259	Intermediate Similarity	NPC227683
0.7248	Intermediate Similarity	NPC82056
0.7248	Intermediate Similarity	NPC134702
0.7248	Intermediate Similarity	NPC87560
0.7225	Intermediate Similarity	NPC203784
0.7225	Intermediate Similarity	NPC170503
0.7225	Intermediate Similarity	NPC470017
0.7225	Intermediate Similarity	NPC126519
0.7222	Intermediate Similarity	NPC77878
0.722	Intermediate Similarity	NPC74575
0.722	Intermediate Similarity	NPC13249
0.7212	Intermediate Similarity	NPC234933
0.7208	Intermediate Similarity	NPC132385
0.7206	Intermediate Similarity	NPC45389
0.7202	Intermediate Similarity	NPC166014
0.7202	Intermediate Similarity	NPC306902
0.7202	Intermediate Similarity	NPC477559
0.7202	Intermediate Similarity	NPC160298
0.7202	Intermediate Similarity	NPC266753
0.7202	Intermediate Similarity	NPC27410
0.7202	Intermediate Similarity	NPC313327
0.7202	Intermediate Similarity	NPC232924
0.72	Intermediate Similarity	NPC260118
0.7198	Intermediate Similarity	NPC120239
0.7192	Intermediate Similarity	NPC21425
0.7192	Intermediate Similarity	NPC214629
0.7189	Intermediate Similarity	NPC148391
0.7186	Intermediate Similarity	NPC142385
0.7182	Intermediate Similarity	NPC157983
0.7182	Intermediate Similarity	NPC118154
0.7175	Intermediate Similarity	NPC476436
0.7164	Intermediate Similarity	NPC215747
0.7164	Intermediate Similarity	NPC192939
0.7157	Intermediate Similarity	NPC86469
0.715	Intermediate Similarity	NPC283810
0.715	Intermediate Similarity	NPC265383
0.7149	Intermediate Similarity	NPC118189
0.7143	Intermediate Similarity	NPC476432
0.7143	Intermediate Similarity	NPC138830
0.7143	Intermediate Similarity	NPC24264
0.7143	Intermediate Similarity	NPC114468
0.7136	Intermediate Similarity	NPC79213
0.713	Intermediate Similarity	NPC220337
0.7129	Intermediate Similarity	NPC115906
0.7129	Intermediate Similarity	NPC100863
0.7128	Intermediate Similarity	NPC324144
0.7122	Intermediate Similarity	NPC237579
0.7116	Intermediate Similarity	NPC46990
0.7115	Intermediate Similarity	NPC470023
0.7115	Intermediate Similarity	NPC174783
0.7114	Intermediate Similarity	NPC121400
0.7113	Intermediate Similarity	NPC475780
0.711	Intermediate Similarity	NPC2905
0.7107	Intermediate Similarity	NPC247389
0.7107	Intermediate Similarity	NPC145832
0.7107	Intermediate Similarity	NPC81218
0.7107	Intermediate Similarity	NPC117188
0.7107	Intermediate Similarity	NPC306555
0.7107	Intermediate Similarity	NPC205421
0.7107	Intermediate Similarity	NPC158376
0.7107	Intermediate Similarity	NPC474931
0.7107	Intermediate Similarity	NPC12053
0.7103	Intermediate Similarity	NPC478075
0.7103	Intermediate Similarity	NPC212123
0.7097	Intermediate Similarity	NPC116178
0.7094	Intermediate Similarity	NPC28425
0.7093	Intermediate Similarity	NPC49547
0.7092	Intermediate Similarity	NPC78222
0.7092	Intermediate Similarity	NPC136508
0.7092	Intermediate Similarity	NPC306843
0.7092	Intermediate Similarity	NPC477563
0.7092	Intermediate Similarity	NPC13504
0.7092	Intermediate Similarity	NPC225774
0.7092	Intermediate Similarity	NPC16805
0.7092	Intermediate Similarity	NPC302527
0.7092	Intermediate Similarity	NPC196447
0.7092	Intermediate Similarity	NPC167546

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 NPC308943 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	810
0.2-0.3	953
0.3-0.4	1637
0.4-0.5	2877
0.5-0.6	2012
0.6-0.7	516
0.7-0.8	43
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8265	Intermediate Similarity	NPD5071	Phase 2
0.8	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD8149	Discontinued
0.7822	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7225	Discontinued
0.7729	Intermediate Similarity	NPD4859	Phase 1
0.761	Intermediate Similarity	NPD6321	Discontinued
0.7592	Intermediate Similarity	NPD5186	Approved
0.7592	Intermediate Similarity	NPD5183	Approved
0.7558	Intermediate Similarity	NPD7278	Phase 2
0.7558	Intermediate Similarity	NPD7279	Phase 2
0.75	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7922	Phase 1
0.7437	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5977	Approved
0.7368	Intermediate Similarity	NPD5978	Approved
0.736	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD4846	Phase 2
0.7241	Intermediate Similarity	NPD7291	Discontinued
0.7214	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6618	Phase 2
0.7158	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5025	Approved
0.715	Intermediate Similarity	NPD6293	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4107	Approved
0.7129	Intermediate Similarity	NPD2968	Approved
0.7129	Intermediate Similarity	NPD2971	Approved
0.7121	Intermediate Similarity	NPD7449	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD8311	Discontinued
0.7095	Intermediate Similarity	NPD3297	Approved
0.7085	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5564	Approved
0.7075	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5997	Discontinued
0.707	Intermediate Similarity	NPD5950	Discontinued
0.7062	Intermediate Similarity	NPD3289	Phase 3
0.7062	Intermediate Similarity	NPD3290	Approved
0.7059	Intermediate Similarity	NPD2899	Discontinued
0.7056	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5488	Discontinued
0.7044	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5919	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7110	Phase 1
0.7028	Intermediate Similarity	NPD4482	Phase 3
0.7026	Intermediate Similarity	NPD6790	Phase 1
0.7019	Intermediate Similarity	NPD7262	Phase 1
0.7009	Intermediate Similarity	NPD6250	Discontinued
0.7005	Intermediate Similarity	NPD6457	Approved
0.7	Intermediate Similarity	NPD3639	Approved
0.7	Intermediate Similarity	NPD8091	Phase 3
0.7	Intermediate Similarity	NPD3640	Phase 3
0.7	Intermediate Similarity	NPD3641	Approved
0.6995	Remote Similarity	NPD7626	Approved
0.6995	Remote Similarity	NPD7627	Approved
0.6995	Remote Similarity	NPD3057	Approved
0.699	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4584	Approved
0.6981	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6297	Approved
0.697	Remote Similarity	NPD7048	Phase 3
0.6963	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3437	Discontinued
0.6946	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4885	Approved
0.6941	Remote Similarity	NPD7301	Phase 3
0.6938	Remote Similarity	NPD6181	Discontinued
0.6935	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.693	Remote Similarity	NPD3298	Approved
0.693	Remote Similarity	NPD4981	Phase 2
0.6927	Remote Similarity	NPD824	Approved
0.6923	Remote Similarity	NPD2490	Approved
0.6923	Remote Similarity	NPD6716	Phase 1
0.6923	Remote Similarity	NPD2488	Approved
0.6919	Remote Similarity	NPD2974	Approved
0.6919	Remote Similarity	NPD2975	Approved
0.6919	Remote Similarity	NPD2973	Approved
0.6916	Remote Similarity	NPD2972	Approved
0.6916	Remote Similarity	NPD3533	Approved
0.6916	Remote Similarity	NPD3448	Approved
0.6916	Remote Similarity	NPD2491	Approved
0.6915	Remote Similarity	NPD7177	Discontinued
0.6912	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6997	Phase 2
0.6887	Remote Similarity	NPD4420	Approved
0.6886	Remote Similarity	NPD7654	Discontinued
0.6881	Remote Similarity	NPD5312	Approved
0.6881	Remote Similarity	NPD5313	Approved
0.6875	Remote Similarity	NPD5928	Phase 1
0.6866	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD3912	Discontinued
0.6857	Remote Similarity	NPD5610	Approved
0.6853	Remote Similarity	NPD3752	Phase 2
0.6849	Remote Similarity	NPD5860	Discontinued
0.6847	Remote Similarity	NPD7479	Phase 2
0.6847	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6853	Approved
0.6845	Remote Similarity	NPD6851	Approved
0.6842	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6625	Approved
0.6837	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4356	Discontinued
0.683	Remote Similarity	NPD3763	Approved
0.6829	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3301	Approved
0.6825	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6612	Phase 2
0.6822	Remote Similarity	NPD4580	Approved
0.6804	Remote Similarity	NPD6875	Approved
0.6804	Remote Similarity	NPD6876	Approved
0.6803	Remote Similarity	NPD7708	Approved
0.6798	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2493	Approved
0.6791	Remote Similarity	NPD3452	Approved
0.6791	Remote Similarity	NPD3450	Approved
0.6791	Remote Similarity	NPD2494	Approved
0.6776	Remote Similarity	NPD6874	Approved
0.6765	Remote Similarity	NPD3920	Phase 2
0.6759	Remote Similarity	NPD5005	Approved
0.6759	Remote Similarity	NPD5006	Approved
0.6756	Remote Similarity	NPD5496	Approved
0.675	Remote Similarity	NPD2821	Approved
0.6742	Remote Similarity	NPD5676	Approved
0.6742	Remote Similarity	NPD683	Approved
0.6733	Remote Similarity	NPD2898	Approved
0.6732	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7569	Approved
0.673	Remote Similarity	NPD7570	Approved
0.6726	Remote Similarity	NPD7559	Phase 2
0.6725	Remote Similarity	NPD7223	Discontinued
0.6725	Remote Similarity	NPD7224	Discontinued
0.6716	Remote Similarity	NPD3793	Phase 3
0.6715	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3964	Approved
0.6713	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7395	Discontinued
0.671	Remote Similarity	NPD4952	Phase 3
0.67	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD1880	Phase 3
0.6698	Remote Similarity	NPD6526	Approved
0.6697	Remote Similarity	NPD5914	Approved
0.6697	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4583	Approved
0.6697	Remote Similarity	NPD4582	Approved
0.6696	Remote Similarity	NPD7907	Approved
0.6695	Remote Similarity	NPD7886	Phase 2
0.6695	Remote Similarity	NPD7885	Phase 2
0.6694	Remote Similarity	NPD7803	Approved
0.6684	Remote Similarity	NPD6385	Approved
0.6684	Remote Similarity	NPD6386	Approved
0.6683	Remote Similarity	NPD5242	Approved
0.6667	Remote Similarity	NPD6493	Phase 3
0.6667	Remote Similarity	NPD3229	Phase 2
0.6667	Remote Similarity	NPD5980	Discovery
0.6667	Remote Similarity	NPD1945	Phase 1
0.6667	Remote Similarity	NPD5457	Discontinued
0.6652	Remote Similarity	NPD3257	Approved
0.6651	Remote Similarity	NPD4004	Approved
0.6651	Remote Similarity	NPD4668	Phase 2
0.6651	Remote Similarity	NPD4002	Approved
0.6651	Remote Similarity	NPD3921	Approved
0.6651	Remote Similarity	NPD5194	Approved
0.6651	Remote Similarity	NPD3922	Approved
0.6651	Remote Similarity	NPD3923	Approved
0.6651	Remote Similarity	NPD5196	Approved
0.6651	Remote Similarity	NPD5197	Approved
0.6651	Remote Similarity	NPD3924	Approved
0.6649	Remote Similarity	NPD6031	Approved
0.6649	Remote Similarity	NPD6030	Approved
0.6639	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6238	Discontinued
0.6636	Remote Similarity	NPD7043	Discontinued
0.6636	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7281	Phase 3
0.6635	Remote Similarity	NPD7280	Phase 3
0.6634	Remote Similarity	NPD4166	Phase 2
0.6634	Remote Similarity	NPD5600	Discontinued
0.6634	Remote Similarity	NPD3965	Phase 1
0.6634	Remote Similarity	NPD5810	Discontinued
0.6624	Remote Similarity	NPD6723	Discontinued
0.6624	Remote Similarity	NPD4373	Phase 2
0.6622	Remote Similarity	NPD7047	Phase 3
0.6621	Remote Similarity	NPD4465	Phase 2
0.6621	Remote Similarity	NPD4467	Phase 2
0.6619	Remote Similarity	NPD4515	Suspended

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