NPASS Compound

Structure

NPC299714 OpenBabel07101719132D 26 28 0 0 1 0 0 0 0 0999 V2000 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 5 6 1 0 0 0 0 5 18 1 0 0 0 0 6 20 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 12 26 1 1 0 0 0 13 20 1 1 0 0 0 14 17 1 0 0 0 0 14 20 1 0 0 0 0 15 18 1 1 0 0 0 15 22 1 0 0 0 0 16 19 1 6 0 0 0 16 23 1 0 0 0 0 17 18 1 1 0 0 0 17 19 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 6 0 0 0 19 24 1 0 0 0 0 20 10 1 6 0 0 0 25 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.07
Volume:	399.898
LogP:	4.184
LogD:	3.218
LogS:	-3.093
# Rotatable Bonds:	3
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.233
Synthetic Accessibility Score:	5.388
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.719
MDCK Permeability:	2.7100077204522677e-05
Pgp-inhibitor:	0.714
Pgp-substrate:	0.058
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.892

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.749
Plasma Protein Binding (PPB):	83.99734497070312%
Volume Distribution (VD):	1.726
Pgp-substrate:	14.666821479797363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.209
CYP1A2-substrate:	0.75
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.766
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.581
CYP3A4-substrate:	0.482

ADMET: Excretion

Clearance (CL):	10.577
Half-life (T1/2):	0.078

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.217
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.811
Rat Oral Acute Toxicity:	0.39
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.815
Carcinogencity:	0.951
Eye Corrosion:	0.843
Eye Irritation:	0.056
Respiratory Toxicity:	0.995

Download Data

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

Natural Product: NPC299714

Natural Product ID:	NPC299714
*Common Name:**	2S-Hydroperoxy-12S-Hydroxyisobromosphaerol
IUPAC Name:	(1S,3S,4S,4aS,6S,8S,8aS,10aS)-1-bromo-8a-(bromomethyl)-6-hydroperoxy-4,10a-dimethyl-8-propan-2-yl-2,3,4a,6,7,8,9,10-octahydro-1H-phenanthrene-3,4-diol
Synonyms:
Standard InCHIKey:	BDSVYFLMKBMVBZ-OQXMJJEBSA-N
Standard InCHI:	InChI=1S/C20H32Br2O4/c1-11(2)13-7-12(26-25)8-14-17-18(3,5-6-20(13,14)10-21)15(22)9-16(23)19(17,4)24/h8,11-13,15-17,23-25H,5-7,9-10H2,1-4H3/t12-,13-,15-,16-,17-,18+,19+,20-/m0/s1
SMILES:	CC(C)[C@@H]1C[C@@H](C=C2[C@H]3[C@](C)(CC[C@]12CBr)[C@H](C[C@@H]([C@@]3(C)O)O)Br)OO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514683
PubChem CID:	44578743
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520219]
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18597527]
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20045651]
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[520640]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[520640]

☑ 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 NPC299714 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	227
0.1-0.2	1863
0.2-0.3	6579
0.3-0.4	17351
0.4-0.5	8384
0.5-0.6	6042
0.6-0.7	1991
0.7-0.8	248
0.8-0.85	2
0.85-0.9	2
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC257510
0.9348	High Similarity	NPC92231
0.9348	High Similarity	NPC34732
0.9213	High Similarity	NPC239453
0.9213	High Similarity	NPC224552
0.9101	High Similarity	NPC188896
0.9032	High Similarity	NPC156912
0.8764	High Similarity	NPC313115
0.8681	High Similarity	NPC131453
0.8571	High Similarity	NPC174273
0.809	Intermediate Similarity	NPC129501
0.7912	Intermediate Similarity	NPC311891
0.7865	Intermediate Similarity	NPC477924
0.7864	Intermediate Similarity	NPC133921
0.7841	Intermediate Similarity	NPC66566
0.7841	Intermediate Similarity	NPC477923
0.7802	Intermediate Similarity	NPC113024
0.7778	Intermediate Similarity	NPC83351
0.7778	Intermediate Similarity	NPC167891
0.7753	Intermediate Similarity	NPC274079
0.7753	Intermediate Similarity	NPC477925
0.7742	Intermediate Similarity	NPC474634
0.7742	Intermediate Similarity	NPC317458
0.7717	Intermediate Similarity	NPC474531
0.7708	Intermediate Similarity	NPC474668
0.7667	Intermediate Similarity	NPC470711
0.7667	Intermediate Similarity	NPC91594
0.7667	Intermediate Similarity	NPC470758
0.766	Intermediate Similarity	NPC238992
0.766	Intermediate Similarity	NPC185568
0.764	Intermediate Similarity	NPC35397
0.764	Intermediate Similarity	NPC474946
0.7634	Intermediate Similarity	NPC47763
0.7634	Intermediate Similarity	NPC30166
0.7609	Intermediate Similarity	NPC236112
0.7609	Intermediate Similarity	NPC287749
0.7604	Intermediate Similarity	NPC470620
0.7579	Intermediate Similarity	NPC318390
0.7556	Intermediate Similarity	NPC470749
0.7556	Intermediate Similarity	NPC265588
0.7553	Intermediate Similarity	NPC207013
0.7553	Intermediate Similarity	NPC253402
0.7553	Intermediate Similarity	NPC159168
0.7528	Intermediate Similarity	NPC476366
0.7528	Intermediate Similarity	NPC477138
0.7528	Intermediate Similarity	NPC201048
0.7528	Intermediate Similarity	NPC243342
0.7527	Intermediate Similarity	NPC47761
0.7527	Intermediate Similarity	NPC476646
0.7526	Intermediate Similarity	NPC133588
0.75	Intermediate Similarity	NPC175145
0.75	Intermediate Similarity	NPC6391
0.75	Intermediate Similarity	NPC242992
0.75	Intermediate Similarity	NPC476610
0.75	Intermediate Similarity	NPC291379
0.75	Intermediate Similarity	NPC475069
0.75	Intermediate Similarity	NPC261266
0.75	Intermediate Similarity	NPC94462
0.75	Intermediate Similarity	NPC237344
0.75	Intermediate Similarity	NPC167706
0.75	Intermediate Similarity	NPC328714
0.7475	Intermediate Similarity	NPC41554
0.7475	Intermediate Similarity	NPC97404
0.7474	Intermediate Similarity	NPC205845
0.7473	Intermediate Similarity	NPC130136
0.7473	Intermediate Similarity	NPC471798
0.7449	Intermediate Similarity	NPC187785
0.7449	Intermediate Similarity	NPC259875
0.7449	Intermediate Similarity	NPC470361
0.7449	Intermediate Similarity	NPC477606
0.7447	Intermediate Similarity	NPC49964
0.7447	Intermediate Similarity	NPC101462
0.7444	Intermediate Similarity	NPC476605
0.7444	Intermediate Similarity	NPC291503
0.7426	Intermediate Similarity	NPC53565
0.7419	Intermediate Similarity	NPC13554
0.7419	Intermediate Similarity	NPC96362
0.7419	Intermediate Similarity	NPC22403
0.7419	Intermediate Similarity	NPC295131
0.7416	Intermediate Similarity	NPC182717
0.7416	Intermediate Similarity	NPC471799
0.7391	Intermediate Similarity	NPC22955
0.7391	Intermediate Similarity	NPC274750
0.7391	Intermediate Similarity	NPC473943
0.7391	Intermediate Similarity	NPC99168
0.7391	Intermediate Similarity	NPC215307
0.7391	Intermediate Similarity	NPC476314
0.7391	Intermediate Similarity	NPC474989
0.7391	Intermediate Similarity	NPC470396
0.7374	Intermediate Similarity	NPC80561
0.7374	Intermediate Similarity	NPC204188
0.7374	Intermediate Similarity	NPC11216
0.7374	Intermediate Similarity	NPC3345
0.7374	Intermediate Similarity	NPC329596
0.7374	Intermediate Similarity	NPC291484
0.7363	Intermediate Similarity	NPC61080
0.7347	Intermediate Similarity	NPC280556
0.7347	Intermediate Similarity	NPC67872
0.734	Intermediate Similarity	NPC249423
0.734	Intermediate Similarity	NPC264245
0.7333	Intermediate Similarity	NPC471797
0.7333	Intermediate Similarity	NPC91858
0.7333	Intermediate Similarity	NPC237510
0.7333	Intermediate Similarity	NPC475793
0.7333	Intermediate Similarity	NPC100334
0.732	Intermediate Similarity	NPC477604
0.7312	Intermediate Similarity	NPC28862
0.7312	Intermediate Similarity	NPC53744
0.7312	Intermediate Similarity	NPC47982
0.7312	Intermediate Similarity	NPC209430
0.7312	Intermediate Similarity	NPC109546
0.7312	Intermediate Similarity	NPC30986
0.7312	Intermediate Similarity	NPC81306
0.7312	Intermediate Similarity	NPC143182
0.7312	Intermediate Similarity	NPC84694
0.7303	Intermediate Similarity	NPC242001
0.7292	Intermediate Similarity	NPC470077
0.7283	Intermediate Similarity	NPC34177
0.7283	Intermediate Similarity	NPC157996
0.7283	Intermediate Similarity	NPC198968
0.7283	Intermediate Similarity	NPC155986
0.7283	Intermediate Similarity	NPC90979
0.7283	Intermediate Similarity	NPC318495
0.7283	Intermediate Similarity	NPC40394
0.7283	Intermediate Similarity	NPC472805
0.7283	Intermediate Similarity	NPC101475
0.7273	Intermediate Similarity	NPC105495
0.7273	Intermediate Similarity	NPC97103
0.7273	Intermediate Similarity	NPC329643
0.7263	Intermediate Similarity	NPC87489
0.7263	Intermediate Similarity	NPC304285
0.7263	Intermediate Similarity	NPC296701
0.7263	Intermediate Similarity	NPC218616
0.7263	Intermediate Similarity	NPC471408
0.7263	Intermediate Similarity	NPC7988
0.7263	Intermediate Similarity	NPC470049
0.7253	Intermediate Similarity	NPC32832
0.7245	Intermediate Similarity	NPC233744
0.7245	Intermediate Similarity	NPC149224
0.7245	Intermediate Similarity	NPC476948
0.7245	Intermediate Similarity	NPC189777
0.7234	Intermediate Similarity	NPC209944
0.7234	Intermediate Similarity	NPC322313
0.7234	Intermediate Similarity	NPC234193
0.7234	Intermediate Similarity	NPC164840
0.7234	Intermediate Similarity	NPC102253
0.7234	Intermediate Similarity	NPC236237
0.7234	Intermediate Similarity	NPC241290
0.7228	Intermediate Similarity	NPC119379
0.7222	Intermediate Similarity	NPC265485
0.7222	Intermediate Similarity	NPC220939
0.7222	Intermediate Similarity	NPC476609
0.7216	Intermediate Similarity	NPC266511
0.7216	Intermediate Similarity	NPC274448
0.7216	Intermediate Similarity	NPC157257
0.7204	Intermediate Similarity	NPC11908
0.7204	Intermediate Similarity	NPC253807
0.7204	Intermediate Similarity	NPC474216
0.7204	Intermediate Similarity	NPC275910
0.7204	Intermediate Similarity	NPC300499
0.7204	Intermediate Similarity	NPC158662
0.7204	Intermediate Similarity	NPC285761
0.7204	Intermediate Similarity	NPC196753
0.7204	Intermediate Similarity	NPC98386
0.7204	Intermediate Similarity	NPC230295
0.72	Intermediate Similarity	NPC295668
0.7191	Intermediate Similarity	NPC92801
0.7191	Intermediate Similarity	NPC34834
0.7191	Intermediate Similarity	NPC145498
0.7188	Intermediate Similarity	NPC82538
0.7188	Intermediate Similarity	NPC134481
0.7188	Intermediate Similarity	NPC237795
0.7188	Intermediate Similarity	NPC475789
0.7184	Intermediate Similarity	NPC72204
0.7184	Intermediate Similarity	NPC288970
0.7174	Intermediate Similarity	NPC107059
0.7174	Intermediate Similarity	NPC106432
0.7174	Intermediate Similarity	NPC321381
0.7174	Intermediate Similarity	NPC321016
0.7174	Intermediate Similarity	NPC189883
0.7174	Intermediate Similarity	NPC253190
0.7174	Intermediate Similarity	NPC27765
0.7174	Intermediate Similarity	NPC120098
0.7174	Intermediate Similarity	NPC300324
0.7174	Intermediate Similarity	NPC122418
0.7174	Intermediate Similarity	NPC290598
0.7174	Intermediate Similarity	NPC265328
0.7174	Intermediate Similarity	NPC240604
0.7174	Intermediate Similarity	NPC30590
0.7174	Intermediate Similarity	NPC106364
0.7174	Intermediate Similarity	NPC476606
0.7159	Intermediate Similarity	NPC244790
0.7159	Intermediate Similarity	NPC208999
0.7158	Intermediate Similarity	NPC474731
0.7158	Intermediate Similarity	NPC7505
0.7158	Intermediate Similarity	NPC82986
0.7158	Intermediate Similarity	NPC6707
0.7158	Intermediate Similarity	NPC474683
0.7158	Intermediate Similarity	NPC209620
0.7158	Intermediate Similarity	NPC474759

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 NPC299714 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	2147
0.2-0.3	4273
0.3-0.4	1863
0.4-0.5	364
0.5-0.6	224
0.6-0.7	60
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7234	Intermediate Similarity	NPD7525	Registered
0.7128	Intermediate Similarity	NPD7645	Phase 2
0.7065	Intermediate Similarity	NPD6942	Approved
0.7065	Intermediate Similarity	NPD7339	Approved
0.6989	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6933	Approved
0.6733	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD8264	Approved
0.66	Remote Similarity	NPD4786	Approved
0.6596	Remote Similarity	NPD6926	Approved
0.6596	Remote Similarity	NPD6924	Approved
0.6569	Remote Similarity	NPD7524	Approved
0.6566	Remote Similarity	NPD3667	Approved
0.6476	Remote Similarity	NPD7515	Phase 2
0.6471	Remote Similarity	NPD3618	Phase 1
0.6442	Remote Similarity	NPD5328	Approved
0.6421	Remote Similarity	NPD4784	Approved
0.6421	Remote Similarity	NPD4785	Approved
0.6396	Remote Similarity	NPD7632	Discontinued
0.6383	Remote Similarity	NPD4243	Approved
0.6364	Remote Similarity	NPD4748	Discontinued
0.6364	Remote Similarity	NPD7509	Discontinued
0.6364	Remote Similarity	NPD6930	Phase 2
0.6364	Remote Similarity	NPD6931	Approved
0.6337	Remote Similarity	NPD6695	Phase 3
0.6327	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6079	Approved
0.6306	Remote Similarity	NPD4159	Approved
0.6275	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7638	Approved
0.6273	Remote Similarity	NPD4225	Approved
0.6263	Remote Similarity	NPD6929	Approved
0.6262	Remote Similarity	NPD4202	Approved
0.6216	Remote Similarity	NPD7639	Approved
0.6216	Remote Similarity	NPD7640	Approved
0.6211	Remote Similarity	NPD7150	Approved
0.6211	Remote Similarity	NPD7152	Approved
0.6211	Remote Similarity	NPD7151	Approved
0.6204	Remote Similarity	NPD7748	Approved
0.62	Remote Similarity	NPD7514	Phase 3
0.62	Remote Similarity	NPD7332	Phase 2
0.6182	Remote Similarity	NPD4755	Approved
0.617	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6922	Approved
0.617	Remote Similarity	NPD6923	Approved
0.6117	Remote Similarity	NPD3666	Approved
0.6117	Remote Similarity	NPD3668	Phase 3
0.6117	Remote Similarity	NPD3665	Phase 1
0.6117	Remote Similarity	NPD3133	Approved
0.6116	Remote Similarity	NPD7115	Discovery
0.6111	Remote Similarity	NPD368	Approved
0.6111	Remote Similarity	NPD6399	Phase 3
0.6106	Remote Similarity	NPD5211	Phase 2
0.6105	Remote Similarity	NPD7144	Approved
0.6105	Remote Similarity	NPD7143	Approved
0.6095	Remote Similarity	NPD7750	Discontinued
0.6091	Remote Similarity	NPD5222	Approved
0.6091	Remote Similarity	NPD5221	Approved
0.6091	Remote Similarity	NPD4697	Phase 3
0.6091	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5285	Approved
0.6071	Remote Similarity	NPD5286	Approved
0.6071	Remote Similarity	NPD4700	Approved
0.6071	Remote Similarity	NPD4696	Approved
0.6061	Remote Similarity	NPD5776	Phase 2
0.6061	Remote Similarity	NPD6932	Approved
0.6061	Remote Similarity	NPD6925	Approved
0.6058	Remote Similarity	NPD6893	Approved
0.6036	Remote Similarity	NPD7902	Approved
0.6036	Remote Similarity	NPD5173	Approved
0.6033	Remote Similarity	NPD6274	Approved
0.602	Remote Similarity	NPD4190	Phase 3
0.602	Remote Similarity	NPD5275	Approved
0.6018	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD5141	Approved
0.5981	Remote Similarity	NPD6051	Approved
0.5981	Remote Similarity	NPD4753	Phase 2
0.598	Remote Similarity	NPD6902	Approved
0.598	Remote Similarity	NPD6898	Phase 1
0.5965	Remote Similarity	NPD5225	Approved
0.5965	Remote Similarity	NPD4633	Approved
0.5965	Remote Similarity	NPD5226	Approved
0.5965	Remote Similarity	NPD5224	Approved
0.5948	Remote Similarity	NPD6402	Approved
0.5948	Remote Similarity	NPD5739	Approved
0.5948	Remote Similarity	NPD6675	Approved
0.5948	Remote Similarity	NPD7128	Approved
0.5941	Remote Similarity	NPD4195	Approved
0.5941	Remote Similarity	NPD6683	Phase 2
0.5932	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5174	Approved
0.5913	Remote Similarity	NPD4754	Approved
0.5913	Remote Similarity	NPD5175	Approved
0.5905	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7516	Approved
0.5882	Remote Similarity	NPD4695	Discontinued
0.5882	Remote Similarity	NPD4634	Approved
0.5877	Remote Similarity	NPD5344	Discontinued
0.5872	Remote Similarity	NPD7087	Discontinued
0.5849	Remote Similarity	NPD4623	Approved
0.5849	Remote Similarity	NPD4519	Discontinued
0.5849	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6899	Approved
0.5847	Remote Similarity	NPD6881	Approved
0.5847	Remote Similarity	NPD7320	Approved
0.5841	Remote Similarity	NPD5290	Discontinued
0.5812	Remote Similarity	NPD4768	Approved
0.5812	Remote Similarity	NPD4767	Approved
0.5806	Remote Similarity	NPD7327	Approved
0.5806	Remote Similarity	NPD7328	Approved
0.5798	Remote Similarity	NPD6373	Approved
0.5798	Remote Similarity	NPD6372	Approved
0.5794	Remote Similarity	NPD8033	Approved
0.5785	Remote Similarity	NPD8297	Approved
0.5769	Remote Similarity	NPD4221	Approved
0.5769	Remote Similarity	NPD4223	Phase 3
0.5766	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7900	Approved
0.5763	Remote Similarity	NPD5697	Approved
0.5763	Remote Similarity	NPD5701	Approved
0.5755	Remote Similarity	NPD5329	Approved
0.5752	Remote Similarity	NPD6084	Phase 2
0.5752	Remote Similarity	NPD6083	Phase 2
0.575	Remote Similarity	NPD6883	Approved
0.575	Remote Similarity	NPD7102	Approved
0.575	Remote Similarity	NPD7290	Approved
0.5738	Remote Similarity	NPD4632	Approved
0.5727	Remote Similarity	NPD6411	Approved
0.5714	Remote Similarity	NPD5128	Approved
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5714	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD4729	Approved
0.5714	Remote Similarity	NPD8377	Approved
0.5714	Remote Similarity	NPD8294	Approved
0.5714	Remote Similarity	NPD4730	Approved
0.5702	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6847	Approved
0.5702	Remote Similarity	NPD6649	Approved
0.5702	Remote Similarity	NPD8130	Phase 1
0.5702	Remote Similarity	NPD6650	Approved
0.5702	Remote Similarity	NPD6617	Approved
0.5702	Remote Similarity	NPD6869	Approved
0.5701	Remote Similarity	NPD5279	Phase 3
0.5686	Remote Similarity	NPD3671	Phase 1
0.5669	Remote Similarity	NPD8380	Approved
0.5669	Remote Similarity	NPD8296	Approved
0.5669	Remote Similarity	NPD8379	Approved
0.5669	Remote Similarity	NPD7503	Approved
0.5669	Remote Similarity	NPD8378	Approved
0.5669	Remote Similarity	NPD8335	Approved
0.5667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6012	Approved
0.5667	Remote Similarity	NPD6013	Approved
0.5667	Remote Similarity	NPD6014	Approved
0.566	Remote Similarity	NPD4197	Approved
0.5656	Remote Similarity	NPD6882	Approved
0.563	Remote Similarity	NPD6412	Phase 2
0.562	Remote Similarity	NPD5249	Phase 3
0.562	Remote Similarity	NPD5247	Approved
0.562	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.562	Remote Similarity	NPD5248	Approved
0.562	Remote Similarity	NPD5251	Approved
0.562	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.562	Remote Similarity	NPD5169	Approved
0.562	Remote Similarity	NPD5135	Approved
0.562	Remote Similarity	NPD5250	Approved
0.5618	Remote Similarity	NPD342	Phase 1
0.5607	Remote Similarity	NPD1696	Phase 3

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