NPASS Compound

Structure

CID268958 OpenBabel06191716072D 26 29 0 0 1 0 0 0 0 0999 V2000 5.1449 -1.2467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6358 -1.1275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8370 -0.6278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2068 -1.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6694 -0.4380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3109 0.6061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1765 0.0172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9343 1.0783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9121 -0.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7236 0.5048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0854 -0.4586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8969 0.9733 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3471 -1.0569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2026 -0.0421 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4055 0.8594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6323 -0.2448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7312 -0.4455 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3303 1.0783 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0778 0.4916 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4191 -0.8528 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8894 1.9115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5503 -1.9159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1503 1.5451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0637 2.2569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1632 -1.5161 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 16 1 0 0 0 0 3 16 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 1 0 0 0 0 8 18 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 19 1 6 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 13 22 2 0 0 0 0 14 16 1 0 0 0 0 14 18 1 6 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 17 4 1 1 0 0 0 18 19 1 1 0 0 0 19 24 1 6 0 0 0 20 25 1 6 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	362.446
LogP:	2.307
LogD:	1.294
LogS:	-4.617
# Rotatable Bonds:	1
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	6.068
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.993
MDCK Permeability:	2.925871012848802e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.101
20% Bioavailability (F20%):	0.238
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.92
Plasma Protein Binding (PPB):	76.13085174560547%
Volume Distribution (VD):	1.123
Pgp-substrate:	28.5441837310791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.833
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.742
CYP2C9-inhibitor:	0.104
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.785
CYP3A4-substrate:	0.528

ADMET: Excretion

Clearance (CL):	2.089
Half-life (T1/2):	0.296

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.256
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.89
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.338
Carcinogencity:	0.677
Eye Corrosion:	0.005
Eye Irritation:	0.141
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC268958

Natural Product ID:	NPC268958
*Common Name:**	Sphaeropsidin D
IUPAC Name:	n.a.
Synonyms:	Sphaeropsidin D
Standard InCHIKey:	RGMZNUAVQHIGNL-WSFBEDDRSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-5-17(4)9-11-13(22)20(25)14-16(2,3)7-6-8-18(14,15(23)26-20)19(11,24)12(21)10-17/h5,9,12,14,21,24-25H,1,6-8,10H2,2-4H3/t12-,14+,17-,18+,19+,20-/m1/s1
SMILES:	C=C[C@@]1(C)C[C@@H](O)[C@]2(C(=C1)C(=O)[C@@]1([C@@H]3[C@@]2(CCCC3(C)C)C(=O)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1834676
PubChem CID:	636779
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO29879	Smardaea	Genus	Pyronemataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21999655]
NPO30074	Diplodia cupressi	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22124378]

☑ 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	10
Others	1

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	10000.0	nM	PMID[511184]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	7500.0	nM	PMID[511184]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[511184]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	3700.0	nM	PMID[511184]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	9600.0	nM	PMID[511184]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	9000.0	nM	PMID[511184]
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	>	10000.0	nM	PMID[511184]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	4800.0	nM	PMID[511184]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	5000.0	nM	PMID[511184]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC25	>	5.0	uM	PMID[511184]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[511184]

☑ 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 NPC268958 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	240
0.1-0.2	1373
0.2-0.3	4085
0.3-0.4	7513
0.4-0.5	11398
0.5-0.6	8731
0.6-0.7	6292
0.7-0.8	2806
0.8-0.85	238
0.85-0.9	17
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC477116
0.9286	High Similarity	NPC27999
0.9174	High Similarity	NPC220705
0.8824	High Similarity	NPC225049
0.8739	High Similarity	NPC470922
0.8718	High Similarity	NPC112038
0.8632	High Similarity	NPC470777
0.8632	High Similarity	NPC469488
0.8618	High Similarity	NPC102316
0.8609	High Similarity	NPC261330
0.8596	High Similarity	NPC472002
0.8596	High Similarity	NPC269530
0.8583	High Similarity	NPC24651
0.8548	High Similarity	NPC168879
0.8547	High Similarity	NPC17772
0.8547	High Similarity	NPC204552
0.8547	High Similarity	NPC251310
0.8547	High Similarity	NPC470776
0.8547	High Similarity	NPC188667
0.8547	High Similarity	NPC297179
0.8537	High Similarity	NPC476852
0.8537	High Similarity	NPC476862
0.8537	High Similarity	NPC476863
0.8534	High Similarity	NPC179626
0.8525	High Similarity	NPC476859
0.8522	High Similarity	NPC51978
0.85	High Similarity	NPC67251
0.8496	Intermediate Similarity	NPC20192
0.8492	Intermediate Similarity	NPC243014
0.8487	Intermediate Similarity	NPC477046
0.8487	Intermediate Similarity	NPC102822
0.8475	Intermediate Similarity	NPC472933
0.8462	Intermediate Similarity	NPC97908
0.8462	Intermediate Similarity	NPC470775
0.8462	Intermediate Similarity	NPC470854
0.8462	Intermediate Similarity	NPC122033
0.8462	Intermediate Similarity	NPC176513
0.8462	Intermediate Similarity	NPC474654
0.8462	Intermediate Similarity	NPC287343
0.8455	Intermediate Similarity	NPC476851
0.843	Intermediate Similarity	NPC476729
0.8421	Intermediate Similarity	NPC5103
0.8417	Intermediate Similarity	NPC312833
0.8403	Intermediate Similarity	NPC107338
0.8403	Intermediate Similarity	NPC109607
0.8393	Intermediate Similarity	NPC181357
0.839	Intermediate Similarity	NPC21326
0.839	Intermediate Similarity	NPC234522
0.8387	Intermediate Similarity	NPC476855
0.8376	Intermediate Similarity	NPC259306
0.8376	Intermediate Similarity	NPC470628
0.8376	Intermediate Similarity	NPC152199
0.8376	Intermediate Similarity	NPC235539
0.8376	Intermediate Similarity	NPC207217
0.8376	Intermediate Similarity	NPC134869
0.8376	Intermediate Similarity	NPC474046
0.8376	Intermediate Similarity	NPC270478
0.8362	Intermediate Similarity	NPC25909
0.8362	Intermediate Similarity	NPC474271
0.8348	Intermediate Similarity	NPC201992
0.8348	Intermediate Similarity	NPC171888
0.8348	Intermediate Similarity	NPC146945
0.8347	Intermediate Similarity	NPC105926
0.8347	Intermediate Similarity	NPC91693
0.8347	Intermediate Similarity	NPC18945
0.8347	Intermediate Similarity	NPC265557
0.8333	Intermediate Similarity	NPC141350
0.832	Intermediate Similarity	NPC254614
0.832	Intermediate Similarity	NPC100390
0.8319	Intermediate Similarity	NPC475775
0.8319	Intermediate Similarity	NPC476529
0.8319	Intermediate Similarity	NPC144854
0.8319	Intermediate Similarity	NPC3316
0.8306	Intermediate Similarity	NPC476854
0.8305	Intermediate Similarity	NPC472927
0.8291	Intermediate Similarity	NPC268238
0.8291	Intermediate Similarity	NPC470919
0.8291	Intermediate Similarity	NPC117712
0.8291	Intermediate Similarity	NPC469877
0.8291	Intermediate Similarity	NPC143268
0.8291	Intermediate Similarity	NPC18547
0.8291	Intermediate Similarity	NPC45218
0.8291	Intermediate Similarity	NPC323821
0.8291	Intermediate Similarity	NPC474906
0.8276	Intermediate Similarity	NPC11252
0.8276	Intermediate Similarity	NPC302146
0.8276	Intermediate Similarity	NPC289312
0.8264	Intermediate Similarity	NPC222688
0.8261	Intermediate Similarity	NPC474567
0.8261	Intermediate Similarity	NPC235014
0.825	Intermediate Similarity	NPC478051
0.825	Intermediate Similarity	NPC109973
0.825	Intermediate Similarity	NPC48692
0.8246	Intermediate Similarity	NPC277017
0.8246	Intermediate Similarity	NPC154608
0.8246	Intermediate Similarity	NPC192813
0.823	Intermediate Similarity	NPC472645
0.822	Intermediate Similarity	NPC40632
0.822	Intermediate Similarity	NPC328374
0.822	Intermediate Similarity	NPC474734
0.822	Intermediate Similarity	NPC96312
0.822	Intermediate Similarity	NPC16081
0.822	Intermediate Similarity	NPC173686
0.822	Intermediate Similarity	NPC251236
0.8205	Intermediate Similarity	NPC208998
0.8205	Intermediate Similarity	NPC198539
0.8205	Intermediate Similarity	NPC7921
0.8205	Intermediate Similarity	NPC469463
0.8205	Intermediate Similarity	NPC469454
0.8205	Intermediate Similarity	NPC469496
0.8205	Intermediate Similarity	NPC49451
0.8198	Intermediate Similarity	NPC470184
0.8197	Intermediate Similarity	NPC469789
0.819	Intermediate Similarity	NPC304180
0.819	Intermediate Similarity	NPC179798
0.8189	Intermediate Similarity	NPC242486
0.8189	Intermediate Similarity	NPC15215
0.8182	Intermediate Similarity	NPC470779
0.8175	Intermediate Similarity	NPC254146
0.8175	Intermediate Similarity	NPC33378
0.8175	Intermediate Similarity	NPC6274
0.8174	Intermediate Similarity	NPC143706
0.8174	Intermediate Similarity	NPC87335
0.8174	Intermediate Similarity	NPC472534
0.816	Intermediate Similarity	NPC264192
0.8158	Intermediate Similarity	NPC230541
0.8151	Intermediate Similarity	NPC472934
0.8151	Intermediate Similarity	NPC473968
0.8151	Intermediate Similarity	NPC469684
0.8145	Intermediate Similarity	NPC473253
0.8145	Intermediate Similarity	NPC470882
0.8145	Intermediate Similarity	NPC473265
0.8142	Intermediate Similarity	NPC296950
0.8142	Intermediate Similarity	NPC146731
0.814	Intermediate Similarity	NPC295885
0.814	Intermediate Similarity	NPC140045
0.814	Intermediate Similarity	NPC596
0.8136	Intermediate Similarity	NPC473798
0.8136	Intermediate Similarity	NPC299849
0.8136	Intermediate Similarity	NPC243354
0.813	Intermediate Similarity	NPC8369
0.812	Intermediate Similarity	NPC205534
0.812	Intermediate Similarity	NPC474516
0.812	Intermediate Similarity	NPC90769
0.8108	Intermediate Similarity	NPC198880
0.8103	Intermediate Similarity	NPC286880
0.8103	Intermediate Similarity	NPC473036
0.8103	Intermediate Similarity	NPC272898
0.8083	Intermediate Similarity	NPC240509
0.808	Intermediate Similarity	NPC295220
0.808	Intermediate Similarity	NPC475636
0.808	Intermediate Similarity	NPC188291
0.807	Intermediate Similarity	NPC102352
0.8067	Intermediate Similarity	NPC213084
0.8067	Intermediate Similarity	NPC190185
0.8067	Intermediate Similarity	NPC478216
0.8065	Intermediate Similarity	NPC293112
0.8065	Intermediate Similarity	NPC477745
0.8062	Intermediate Similarity	NPC141215
0.8062	Intermediate Similarity	NPC251998
0.8062	Intermediate Similarity	NPC471089
0.8062	Intermediate Similarity	NPC190065
0.8053	Intermediate Similarity	NPC275583
0.8051	Intermediate Similarity	NPC255017
0.8051	Intermediate Similarity	NPC159333
0.8051	Intermediate Similarity	NPC472926
0.8051	Intermediate Similarity	NPC478212
0.8051	Intermediate Similarity	NPC56448
0.8051	Intermediate Similarity	NPC194273
0.8049	Intermediate Similarity	NPC120724
0.8036	Intermediate Similarity	NPC115862
0.8034	Intermediate Similarity	NPC472928
0.8034	Intermediate Similarity	NPC317107
0.8034	Intermediate Similarity	NPC471243
0.8034	Intermediate Similarity	NPC188738
0.8033	Intermediate Similarity	NPC470921
0.8033	Intermediate Similarity	NPC472001
0.8033	Intermediate Similarity	NPC67569
0.8017	Intermediate Similarity	NPC474242
0.8017	Intermediate Similarity	NPC77947
0.8017	Intermediate Similarity	NPC286174
0.8016	Intermediate Similarity	NPC309096
0.8016	Intermediate Similarity	NPC473593
0.8016	Intermediate Similarity	NPC54614
0.8016	Intermediate Similarity	NPC470880
0.8	Intermediate Similarity	NPC218970
0.8	Intermediate Similarity	NPC13713
0.8	Intermediate Similarity	NPC473590
0.8	Intermediate Similarity	NPC23046
0.8	Intermediate Similarity	NPC134430
0.8	Intermediate Similarity	NPC476008
0.8	Intermediate Similarity	NPC470780
0.8	Intermediate Similarity	NPC58662
0.8	Intermediate Similarity	NPC471854
0.7984	Intermediate Similarity	NPC81736
0.7984	Intermediate Similarity	NPC172154
0.7984	Intermediate Similarity	NPC262813
0.7983	Intermediate Similarity	NPC247069
0.7982	Intermediate Similarity	NPC258532
0.7969	Intermediate Similarity	NPC478151

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 NPC268958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1618
0.2-0.3	3651
0.3-0.4	2362
0.4-0.5	743
0.5-0.6	312
0.6-0.7	150
0.7-0.8	94
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.813	Intermediate Similarity	NPD7492	Approved
0.8099	Intermediate Similarity	NPD6054	Approved
0.8099	Intermediate Similarity	NPD6319	Approved
0.8065	Intermediate Similarity	NPD6616	Approved
0.8033	Intermediate Similarity	NPD6016	Approved
0.8033	Intermediate Similarity	NPD6015	Approved
0.8	Intermediate Similarity	NPD7078	Approved
0.7967	Intermediate Similarity	NPD5988	Approved
0.7967	Intermediate Similarity	NPD6370	Approved
0.7937	Intermediate Similarity	NPD7736	Approved
0.7851	Intermediate Similarity	NPD6009	Approved
0.7845	Intermediate Similarity	NPD5697	Approved
0.7815	Intermediate Similarity	NPD6882	Approved
0.7805	Intermediate Similarity	NPD6059	Approved
0.7778	Intermediate Similarity	NPD6881	Approved
0.7778	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6899	Approved
0.776	Intermediate Similarity	NPD8328	Phase 3
0.775	Intermediate Similarity	NPD4632	Approved
0.7731	Intermediate Similarity	NPD6649	Approved
0.7731	Intermediate Similarity	NPD6650	Approved
0.7717	Intermediate Similarity	NPD8293	Discontinued
0.7712	Intermediate Similarity	NPD6012	Approved
0.7712	Intermediate Similarity	NPD6014	Approved
0.7712	Intermediate Similarity	NPD6013	Approved
0.7705	Intermediate Similarity	NPD7115	Discovery
0.7699	Intermediate Similarity	NPD4225	Approved
0.7667	Intermediate Similarity	NPD8297	Approved
0.7647	Intermediate Similarity	NPD7290	Approved
0.7647	Intermediate Similarity	NPD6883	Approved
0.7647	Intermediate Similarity	NPD7102	Approved
0.7647	Intermediate Similarity	NPD4634	Approved
0.7627	Intermediate Similarity	NPD6011	Approved
0.7607	Intermediate Similarity	NPD6675	Approved
0.7607	Intermediate Similarity	NPD6402	Approved
0.7607	Intermediate Similarity	NPD7128	Approved
0.7607	Intermediate Similarity	NPD5739	Approved
0.7583	Intermediate Similarity	NPD6617	Approved
0.7583	Intermediate Similarity	NPD6847	Approved
0.7583	Intermediate Similarity	NPD8130	Phase 1
0.7583	Intermediate Similarity	NPD6869	Approved
0.7563	Intermediate Similarity	NPD6372	Approved
0.7563	Intermediate Similarity	NPD6373	Approved
0.7561	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD5211	Phase 2
0.7479	Intermediate Similarity	NPD7320	Approved
0.746	Intermediate Similarity	NPD5983	Phase 2
0.7417	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5141	Approved
0.7344	Intermediate Similarity	NPD7604	Phase 2
0.7333	Intermediate Similarity	NPD6686	Approved
0.7328	Intermediate Similarity	NPD5285	Approved
0.7328	Intermediate Similarity	NPD5286	Approved
0.7328	Intermediate Similarity	NPD4696	Approved
0.7311	Intermediate Similarity	NPD6008	Approved
0.7252	Intermediate Similarity	NPD6033	Approved
0.7241	Intermediate Similarity	NPD5696	Approved
0.7231	Intermediate Similarity	NPD6336	Discontinued
0.7213	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5224	Approved
0.7203	Intermediate Similarity	NPD5225	Approved
0.7203	Intermediate Similarity	NPD4633	Approved
0.7203	Intermediate Similarity	NPD5226	Approved
0.72	Intermediate Similarity	NPD6274	Approved
0.7197	Intermediate Similarity	NPD7319	Approved
0.7188	Intermediate Similarity	NPD8516	Approved
0.7188	Intermediate Similarity	NPD8515	Approved
0.7188	Intermediate Similarity	NPD8517	Approved
0.7188	Intermediate Similarity	NPD8513	Phase 3
0.7165	Intermediate Similarity	NPD7100	Approved
0.7165	Intermediate Similarity	NPD7101	Approved
0.7155	Intermediate Similarity	NPD4755	Approved
0.7154	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD5174	Approved
0.7119	Intermediate Similarity	NPD5223	Approved
0.7105	Intermediate Similarity	NPD5779	Approved
0.7105	Intermediate Similarity	NPD5778	Approved
0.7099	Intermediate Similarity	NPD7507	Approved
0.7087	Intermediate Similarity	NPD6335	Approved
0.7087	Intermediate Similarity	NPD6313	Approved
0.7087	Intermediate Similarity	NPD6314	Approved
0.7069	Intermediate Similarity	NPD5222	Approved
0.7069	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5221	Approved
0.7054	Intermediate Similarity	NPD6921	Approved
0.7054	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5282	Discontinued
0.7034	Intermediate Similarity	NPD7639	Approved
0.7034	Intermediate Similarity	NPD4700	Approved
0.7034	Intermediate Similarity	NPD7640	Approved
0.7009	Intermediate Similarity	NPD6084	Phase 2
0.7009	Intermediate Similarity	NPD6083	Phase 2
0.7009	Intermediate Similarity	NPD5173	Approved
0.6992	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4629	Approved
0.6983	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5210	Approved
0.6967	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6412	Phase 2
0.6949	Remote Similarity	NPD7638	Approved
0.6935	Remote Similarity	NPD6371	Approved
0.6929	Remote Similarity	NPD6868	Approved
0.6923	Remote Similarity	NPD4697	Phase 3
0.6917	Remote Similarity	NPD8074	Phase 3
0.6911	Remote Similarity	NPD4730	Approved
0.6911	Remote Similarity	NPD4729	Approved
0.6889	Remote Similarity	NPD5956	Approved
0.688	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6411	Approved
0.687	Remote Similarity	NPD6079	Approved
0.6864	Remote Similarity	NPD7902	Approved
0.6838	Remote Similarity	NPD5695	Phase 3
0.6838	Remote Similarity	NPD7260	Phase 2
0.6833	Remote Similarity	NPD5344	Discontinued
0.6829	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3573	Approved
0.681	Remote Similarity	NPD6399	Phase 3
0.68	Remote Similarity	NPD5251	Approved
0.68	Remote Similarity	NPD5250	Approved
0.68	Remote Similarity	NPD5249	Phase 3
0.68	Remote Similarity	NPD5248	Approved
0.68	Remote Similarity	NPD5247	Approved
0.6794	Remote Similarity	NPD6908	Approved
0.6794	Remote Similarity	NPD6909	Approved
0.6786	Remote Similarity	NPD1694	Approved
0.6774	Remote Similarity	NPD5128	Approved
0.6752	Remote Similarity	NPD7748	Approved
0.6748	Remote Similarity	NPD4768	Approved
0.6748	Remote Similarity	NPD4767	Approved
0.6746	Remote Similarity	NPD5216	Approved
0.6746	Remote Similarity	NPD5215	Approved
0.6746	Remote Similarity	NPD5217	Approved
0.6726	Remote Similarity	NPD3618	Phase 1
0.6726	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7983	Approved
0.6724	Remote Similarity	NPD7515	Phase 2
0.6721	Remote Similarity	NPD4754	Approved
0.6714	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5328	Approved
0.6696	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6101	Approved
0.6692	Remote Similarity	NPD7327	Approved
0.6692	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD6334	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6333	Approved
0.6641	Remote Similarity	NPD7516	Approved
0.6639	Remote Similarity	NPD7632	Discontinued
0.6614	Remote Similarity	NPD5127	Approved
0.661	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7900	Approved
0.6609	Remote Similarity	NPD6672	Approved
0.6609	Remote Similarity	NPD5737	Approved
0.6581	Remote Similarity	NPD7637	Suspended
0.6562	Remote Similarity	NPD6053	Discontinued
0.6552	Remote Similarity	NPD4753	Phase 2
0.6541	Remote Similarity	NPD8033	Approved
0.6525	Remote Similarity	NPD4202	Approved
0.6515	Remote Similarity	NPD4522	Approved
0.6508	Remote Similarity	NPD5168	Approved
0.6496	Remote Similarity	NPD5785	Approved
0.6486	Remote Similarity	NPD4695	Discontinued
0.6475	Remote Similarity	NPD6648	Approved
0.6466	Remote Similarity	NPD8294	Approved
0.6466	Remote Similarity	NPD8377	Approved
0.6462	Remote Similarity	NPD5167	Approved
0.6444	Remote Similarity	NPD6067	Discontinued
0.6441	Remote Similarity	NPD5693	Phase 1
0.6418	Remote Similarity	NPD8380	Approved
0.6418	Remote Similarity	NPD8335	Approved
0.6418	Remote Similarity	NPD8379	Approved
0.6418	Remote Similarity	NPD8296	Approved
0.6418	Remote Similarity	NPD8378	Approved
0.6417	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6080	Approved
0.641	Remote Similarity	NPD6904	Approved
0.641	Remote Similarity	NPD6673	Approved
0.6393	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD8133	Approved
0.6372	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD3667	Approved
0.6364	Remote Similarity	NPD7839	Suspended
0.6356	Remote Similarity	NPD46	Approved
0.6356	Remote Similarity	NPD6698	Approved
0.6348	Remote Similarity	NPD5363	Approved
0.6348	Remote Similarity	NPD1696	Phase 3
0.6347	Remote Similarity	NPD8407	Phase 2
0.6319	Remote Similarity	NPD7799	Discontinued
0.6303	Remote Similarity	NPD5281	Approved
0.6303	Remote Similarity	NPD5694	Approved
0.6303	Remote Similarity	NPD5284	Approved
0.6299	Remote Similarity	NPD6614	Approved
0.6293	Remote Similarity	NPD6409	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