NPASS Compound

Structure

NPC34732 OpenBabel07101718292D 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 3.4641 1.0000 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 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 -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 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 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 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 -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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 12 20 1 1 0 0 0 13 16 1 0 0 0 0 13 26 1 1 0 0 0 14 18 1 1 0 0 0 14 22 1 0 0 0 0 15 19 1 1 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 6 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:	4.395
LogD:	3.327
LogS:	-3.946
# 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:	0.235
Synthetic Accessibility Score:	5.733
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:	-4.934
MDCK Permeability:	2.8381999072735198e-05
Pgp-inhibitor:	0.067
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.111
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.758
Plasma Protein Binding (PPB):	88.96858978271484%
Volume Distribution (VD):	1.141
Pgp-substrate:	12.961398124694824%

ADMET: Metabolism

CYP1A2-inhibitor:	0.172
CYP1A2-substrate:	0.477
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.712
CYP2C9-inhibitor:	0.287
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.649
CYP3A4-substrate:	0.407

ADMET: Excretion

Clearance (CL):	4.55
Half-life (T1/2):	0.128

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.28
AMES Toxicity:	0.661
Rat Oral Acute Toxicity:	0.315
Maximum Recommended Daily Dose:	0.058
Skin Sensitization:	0.603
Carcinogencity:	0.573
Eye Corrosion:	0.953
Eye Irritation:	0.267
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC34732

Natural Product ID:	NPC34732
*Common Name:**	1S-Hydroperoxy-12R-Hydroxy-Bromosphaerol-B
IUPAC Name:	(1S,3R,4S,4aS,4bS,5S,8R,8aS,10aS)-1-bromo-8a-(bromomethyl)-5-hydroperoxy-4,10a-dimethyl-8-propan-2-yl-2,3,4a,4b,5,8,9,10-octahydro-1H-phenanthrene-3,4-diol
Synonyms:
Standard InCHIKey:	SLASZMTUABGCGQ-CFAVNGNNSA-N
Standard InCHI:	InChI=1S/C20H32Br2O4/c1-11(2)12-5-6-13(26-25)16-17-18(3,7-8-20(12,16)10-21)14(22)9-15(23)19(17,4)24/h5-6,11-17,23-25H,7-10H2,1-4H3/t12-,13-,14-,15+,16-,17-,18+,19+,20-/m0/s1
SMILES:	CC(C)[C@@H]1C=C[C@@H]([C@H]2[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:	CHEMBL603906
PubChem CID:	24850617
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
IC50	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	40000.0	nM	PMID[537373]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	31000.0	nM	PMID[537373]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	30000.0	nM	PMID[537373]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	22000.0	nM	PMID[537373]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	32000.0	nM	PMID[537373]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25000.0	nM	PMID[537373]

☑ 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 NPC34732 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	238
0.1-0.2	1913
0.2-0.3	6585
0.3-0.4	16818
0.4-0.5	8777
0.5-0.6	6385
0.6-0.7	1791
0.7-0.8	178
0.8-0.85	4
0.85-0.9	1
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC92231
0.967	High Similarity	NPC156912
0.9348	High Similarity	NPC257510
0.9348	High Similarity	NPC299714
0.9222	High Similarity	NPC239453
0.9222	High Similarity	NPC224552
0.8901	High Similarity	NPC131453
0.8495	Intermediate Similarity	NPC188896
0.837	Intermediate Similarity	NPC313115
0.8191	Intermediate Similarity	NPC174273
0.8111	Intermediate Similarity	NPC129501
0.7917	Intermediate Similarity	NPC133588
0.7885	Intermediate Similarity	NPC133921
0.7826	Intermediate Similarity	NPC287749
0.7742	Intermediate Similarity	NPC476646
0.7732	Intermediate Similarity	NPC474668
0.7717	Intermediate Similarity	NPC476610
0.7692	Intermediate Similarity	NPC130136
0.7677	Intermediate Similarity	NPC97404
0.7677	Intermediate Similarity	NPC41554
0.7653	Intermediate Similarity	NPC187785
0.7653	Intermediate Similarity	NPC259875
0.7634	Intermediate Similarity	NPC96362
0.7576	Intermediate Similarity	NPC80561
0.7576	Intermediate Similarity	NPC329596
0.7576	Intermediate Similarity	NPC204188
0.7576	Intermediate Similarity	NPC11216
0.7576	Intermediate Similarity	NPC3345
0.7576	Intermediate Similarity	NPC291484
0.7553	Intermediate Similarity	NPC249423
0.7553	Intermediate Similarity	NPC311891
0.7526	Intermediate Similarity	NPC299068
0.7526	Intermediate Similarity	NPC261266
0.7526	Intermediate Similarity	NPC237344
0.75	Intermediate Similarity	NPC471798
0.75	Intermediate Similarity	NPC275671
0.7475	Intermediate Similarity	NPC470361
0.7475	Intermediate Similarity	NPC97103
0.7475	Intermediate Similarity	NPC109744
0.7449	Intermediate Similarity	NPC189777
0.7449	Intermediate Similarity	NPC233744
0.7449	Intermediate Similarity	NPC474657
0.7449	Intermediate Similarity	NPC470620
0.7449	Intermediate Similarity	NPC186145
0.7447	Intermediate Similarity	NPC113024
0.7447	Intermediate Similarity	NPC471266
0.7447	Intermediate Similarity	NPC95124
0.7423	Intermediate Similarity	NPC470360
0.7423	Intermediate Similarity	NPC318390
0.7419	Intermediate Similarity	NPC83351
0.7419	Intermediate Similarity	NPC167891
0.74	Intermediate Similarity	NPC473956
0.74	Intermediate Similarity	NPC475751
0.7396	Intermediate Similarity	NPC185605
0.7396	Intermediate Similarity	NPC207013
0.7396	Intermediate Similarity	NPC253402
0.7396	Intermediate Similarity	NPC159168
0.7391	Intermediate Similarity	NPC477925
0.7391	Intermediate Similarity	NPC274079
0.7391	Intermediate Similarity	NPC253190
0.7379	Intermediate Similarity	NPC288970
0.7374	Intermediate Similarity	NPC212596
0.7374	Intermediate Similarity	NPC4574
0.7374	Intermediate Similarity	NPC280556
0.7374	Intermediate Similarity	NPC475605
0.7374	Intermediate Similarity	NPC475664
0.7368	Intermediate Similarity	NPC471270
0.7363	Intermediate Similarity	NPC475793
0.7363	Intermediate Similarity	NPC237510
0.7353	Intermediate Similarity	NPC127718
0.7353	Intermediate Similarity	NPC65402
0.7347	Intermediate Similarity	NPC94462
0.7347	Intermediate Similarity	NPC6391
0.7347	Intermediate Similarity	NPC139724
0.732	Intermediate Similarity	NPC238992
0.7312	Intermediate Similarity	NPC470758
0.7312	Intermediate Similarity	NPC477924
0.7312	Intermediate Similarity	NPC91594
0.7312	Intermediate Similarity	NPC470711
0.7308	Intermediate Similarity	NPC477226
0.73	Intermediate Similarity	NPC138974
0.73	Intermediate Similarity	NPC115607
0.73	Intermediate Similarity	NPC105495
0.73	Intermediate Similarity	NPC101886
0.73	Intermediate Similarity	NPC329643
0.7292	Intermediate Similarity	NPC47763
0.7292	Intermediate Similarity	NPC30166
0.7283	Intermediate Similarity	NPC66566
0.7283	Intermediate Similarity	NPC291503
0.7283	Intermediate Similarity	NPC476605
0.7283	Intermediate Similarity	NPC477923
0.7283	Intermediate Similarity	NPC32832
0.7282	Intermediate Similarity	NPC8774
0.7273	Intermediate Similarity	NPC476948
0.7273	Intermediate Similarity	NPC304083
0.7263	Intermediate Similarity	NPC236112
0.7263	Intermediate Similarity	NPC236707
0.7255	Intermediate Similarity	NPC119379
0.7255	Intermediate Similarity	NPC310013
0.7253	Intermediate Similarity	NPC182717
0.7234	Intermediate Similarity	NPC11908
0.7228	Intermediate Similarity	NPC191323
0.7228	Intermediate Similarity	NPC470390
0.7228	Intermediate Similarity	NPC192437
0.7228	Intermediate Similarity	NPC245410
0.7228	Intermediate Similarity	NPC270511
0.7228	Intermediate Similarity	NPC295668
0.7228	Intermediate Similarity	NPC14380
0.7216	Intermediate Similarity	NPC474634
0.7216	Intermediate Similarity	NPC141941
0.7216	Intermediate Similarity	NPC134481
0.7216	Intermediate Similarity	NPC317458
0.7216	Intermediate Similarity	NPC193870
0.7212	Intermediate Similarity	NPC98457
0.7212	Intermediate Similarity	NPC72204
0.7212	Intermediate Similarity	NPC103165
0.7212	Intermediate Similarity	NPC210717
0.7212	Intermediate Similarity	NPC227583
0.7212	Intermediate Similarity	NPC12103
0.7204	Intermediate Similarity	NPC106432
0.7204	Intermediate Similarity	NPC470749
0.7204	Intermediate Similarity	NPC265588
0.72	Intermediate Similarity	NPC475817
0.7188	Intermediate Similarity	NPC47761
0.7188	Intermediate Similarity	NPC474531
0.7174	Intermediate Similarity	NPC243342
0.7174	Intermediate Similarity	NPC477138
0.7174	Intermediate Similarity	NPC476366
0.7174	Intermediate Similarity	NPC91858
0.7174	Intermediate Similarity	NPC306727
0.7174	Intermediate Similarity	NPC201048
0.7172	Intermediate Similarity	NPC476217
0.7172	Intermediate Similarity	NPC175145
0.7172	Intermediate Similarity	NPC6605
0.7172	Intermediate Similarity	NPC475069
0.7157	Intermediate Similarity	NPC210268
0.7143	Intermediate Similarity	NPC127606
0.7143	Intermediate Similarity	NPC167706
0.7143	Intermediate Similarity	NPC471271
0.7143	Intermediate Similarity	NPC475798
0.7143	Intermediate Similarity	NPC185568
0.7143	Intermediate Similarity	NPC470077
0.7143	Intermediate Similarity	NPC124172
0.7143	Intermediate Similarity	NPC83702
0.7143	Intermediate Similarity	NPC205845
0.7143	Intermediate Similarity	NPC471268
0.7129	Intermediate Similarity	NPC16265
0.7115	Intermediate Similarity	NPC53565
0.7113	Intermediate Similarity	NPC296701
0.7113	Intermediate Similarity	NPC49964
0.7113	Intermediate Similarity	NPC87489
0.7113	Intermediate Similarity	NPC218616
0.7113	Intermediate Similarity	NPC50964
0.7113	Intermediate Similarity	NPC7988
0.7097	Intermediate Similarity	NPC35397
0.7097	Intermediate Similarity	NPC474946
0.7083	Intermediate Similarity	NPC236237
0.7083	Intermediate Similarity	NPC322313
0.7083	Intermediate Similarity	NPC102253
0.7083	Intermediate Similarity	NPC295131
0.7083	Intermediate Similarity	NPC13554
0.7071	Intermediate Similarity	NPC290731
0.7065	Intermediate Similarity	NPC476609
0.7065	Intermediate Similarity	NPC95165
0.7065	Intermediate Similarity	NPC471799
0.7064	Intermediate Similarity	NPC160843
0.7059	Intermediate Similarity	NPC92885
0.7059	Intermediate Similarity	NPC77796
0.7059	Intermediate Similarity	NPC476226
0.7053	Intermediate Similarity	NPC300499
0.7053	Intermediate Similarity	NPC274750
0.7053	Intermediate Similarity	NPC215307
0.7053	Intermediate Similarity	NPC148977
0.7048	Intermediate Similarity	NPC471903
0.7048	Intermediate Similarity	NPC90583
0.7041	Intermediate Similarity	NPC85095
0.7041	Intermediate Similarity	NPC477818
0.7041	Intermediate Similarity	NPC211135
0.7041	Intermediate Similarity	NPC110778
0.7041	Intermediate Similarity	NPC216420
0.7041	Intermediate Similarity	NPC470558
0.7041	Intermediate Similarity	NPC82623
0.703	Intermediate Similarity	NPC67872
0.7021	Intermediate Similarity	NPC63958
0.7021	Intermediate Similarity	NPC61080
0.7021	Intermediate Similarity	NPC476606
0.7019	Intermediate Similarity	NPC305160
0.7019	Intermediate Similarity	NPC477605
0.701	Intermediate Similarity	NPC23852
0.701	Intermediate Similarity	NPC264245
0.701	Intermediate Similarity	NPC209620
0.701	Intermediate Similarity	NPC242350
0.7	Intermediate Similarity	NPC152808
0.7	Intermediate Similarity	NPC166607
0.7	Intermediate Similarity	NPC201273
0.7	Intermediate Similarity	NPC269058
0.7	Intermediate Similarity	NPC24277
0.7	Intermediate Similarity	NPC71520
0.7	Intermediate Similarity	NPC293287
0.6989	Remote Similarity	NPC100334

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 NPC34732 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	2242
0.2-0.3	4247
0.3-0.4	1793
0.4-0.5	372
0.5-0.6	230
0.6-0.7	39
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
0.7083	Intermediate Similarity	NPD7525	Registered
0.6804	Remote Similarity	NPD7645	Phase 2
0.6602	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6942	Approved
0.6562	Remote Similarity	NPD7339	Approved
0.6495	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7524	Approved
0.6429	Remote Similarity	NPD7632	Discontinued
0.6392	Remote Similarity	NPD8264	Approved
0.6327	Remote Similarity	NPD6933	Approved
0.6311	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD7639	Approved
0.6238	Remote Similarity	NPD6931	Approved
0.6238	Remote Similarity	NPD7332	Phase 2
0.6238	Remote Similarity	NPD6930	Phase 2
0.6238	Remote Similarity	NPD7514	Phase 3
0.6214	Remote Similarity	NPD6695	Phase 3
0.6204	Remote Similarity	NPD6079	Approved
0.6204	Remote Similarity	NPD7515	Phase 2
0.619	Remote Similarity	NPD3618	Phase 1
0.6186	Remote Similarity	NPD4634	Approved
0.6168	Remote Similarity	NPD5328	Approved
0.6154	Remote Similarity	NPD4786	Approved
0.6147	Remote Similarity	NPD4202	Approved
0.614	Remote Similarity	NPD5211	Phase 2
0.6139	Remote Similarity	NPD6929	Approved
0.6122	Remote Similarity	NPD4784	Approved
0.6122	Remote Similarity	NPD6924	Approved
0.6122	Remote Similarity	NPD4785	Approved
0.6122	Remote Similarity	NPD6926	Approved
0.6117	Remote Similarity	NPD3667	Approved
0.6106	Remote Similarity	NPD5286	Approved
0.6106	Remote Similarity	NPD5285	Approved
0.6106	Remote Similarity	NPD4696	Approved
0.6102	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6932	Approved
0.6082	Remote Similarity	NPD4243	Approved
0.6078	Remote Similarity	NPD7509	Discontinued
0.6071	Remote Similarity	NPD4755	Approved
0.6053	Remote Similarity	NPD5344	Discontinued
0.6053	Remote Similarity	NPD5223	Approved
0.6048	Remote Similarity	NPD7516	Approved
0.6042	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7145	Approved
0.604	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD5141	Approved
0.6033	Remote Similarity	NPD4632	Approved
0.6019	Remote Similarity	NPD6902	Approved
0.6017	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD5224	Approved
0.5982	Remote Similarity	NPD5221	Approved
0.5982	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5222	Approved
0.5981	Remote Similarity	NPD7750	Discontinued
0.5978	Remote Similarity	NPD368	Approved
0.5968	Remote Similarity	NPD7328	Approved
0.5968	Remote Similarity	NPD7327	Approved
0.5965	Remote Similarity	NPD4700	Approved
0.5952	Remote Similarity	NPD7503	Approved
0.5948	Remote Similarity	NPD5174	Approved
0.5948	Remote Similarity	NPD5175	Approved
0.5946	Remote Similarity	NPD7748	Approved
0.5943	Remote Similarity	NPD6893	Approved
0.5941	Remote Similarity	NPD6925	Approved
0.5941	Remote Similarity	NPD5776	Phase 2
0.5935	Remote Similarity	NPD6274	Approved
0.5929	Remote Similarity	NPD5173	Approved
0.5929	Remote Similarity	NPD7902	Approved
0.5922	Remote Similarity	NPD4748	Discontinued
0.5918	Remote Similarity	NPD7151	Approved
0.5918	Remote Similarity	NPD7150	Approved
0.5918	Remote Similarity	NPD7152	Approved
0.5913	Remote Similarity	NPD4159	Approved
0.5887	Remote Similarity	NPD7115	Discovery
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD6899	Approved
0.5877	Remote Similarity	NPD4225	Approved
0.5873	Remote Similarity	NPD8294	Approved
0.5873	Remote Similarity	NPD8377	Approved
0.5865	Remote Similarity	NPD6898	Phase 1
0.5856	Remote Similarity	NPD6399	Phase 3
0.5849	Remote Similarity	NPD3666	Approved
0.5849	Remote Similarity	NPD3133	Approved
0.5849	Remote Similarity	NPD3665	Phase 1
0.5847	Remote Similarity	NPD6402	Approved
0.5847	Remote Similarity	NPD7128	Approved
0.5847	Remote Similarity	NPD6675	Approved
0.5847	Remote Similarity	NPD5739	Approved
0.5841	Remote Similarity	NPD4697	Phase 3
0.5833	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD8380	Approved
0.5827	Remote Similarity	NPD8033	Approved
0.5827	Remote Similarity	NPD8379	Approved
0.5827	Remote Similarity	NPD8378	Approved
0.5827	Remote Similarity	NPD8296	Approved
0.5827	Remote Similarity	NPD8335	Approved
0.5825	Remote Similarity	NPD4195	Approved
0.5825	Remote Similarity	NPD6683	Phase 2
0.582	Remote Similarity	NPD8297	Approved
0.5816	Remote Similarity	NPD7143	Approved
0.5816	Remote Similarity	NPD7144	Approved
0.5812	Remote Similarity	NPD4754	Approved
0.5798	Remote Similarity	NPD6412	Phase 2
0.5798	Remote Similarity	NPD5697	Approved
0.5785	Remote Similarity	NPD6883	Approved
0.5785	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD7290	Approved
0.5785	Remote Similarity	NPD7102	Approved
0.5766	Remote Similarity	NPD7087	Discontinued
0.576	Remote Similarity	NPD6009	Approved
0.575	Remote Similarity	NPD4729	Approved
0.575	Remote Similarity	NPD6011	Approved
0.575	Remote Similarity	NPD6686	Approved
0.575	Remote Similarity	NPD4730	Approved
0.575	Remote Similarity	NPD7320	Approved
0.5748	Remote Similarity	NPD6054	Approved
0.5748	Remote Similarity	NPD6319	Approved
0.5743	Remote Similarity	NPD4190	Phase 3
0.5743	Remote Similarity	NPD5275	Approved
0.5741	Remote Similarity	NPD4519	Discontinued
0.5741	Remote Similarity	NPD4623	Approved
0.5739	Remote Similarity	NPD5290	Discontinued
0.5738	Remote Similarity	NPD6847	Approved
0.5738	Remote Similarity	NPD6650	Approved
0.5738	Remote Similarity	NPD6617	Approved
0.5738	Remote Similarity	NPD6649	Approved
0.5738	Remote Similarity	NPD8130	Phase 1
0.5738	Remote Similarity	NPD6869	Approved
0.5727	Remote Similarity	NPD6051	Approved
0.5727	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD6922	Approved
0.5714	Remote Similarity	NPD6923	Approved
0.5714	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD4768	Approved
0.5702	Remote Similarity	NPD6372	Approved
0.5702	Remote Similarity	NPD6013	Approved
0.5702	Remote Similarity	NPD6373	Approved
0.5702	Remote Similarity	NPD6012	Approved
0.5702	Remote Similarity	NPD6014	Approved
0.5701	Remote Similarity	NPD3668	Phase 3
0.5691	Remote Similarity	NPD6882	Approved
0.569	Remote Similarity	NPD6648	Approved
0.5667	Remote Similarity	NPD5701	Approved
0.5664	Remote Similarity	NPD7900	Approved
0.5664	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD6370	Approved
0.5656	Remote Similarity	NPD5247	Approved
0.5656	Remote Similarity	NPD5135	Approved
0.5656	Remote Similarity	NPD5249	Phase 3
0.5656	Remote Similarity	NPD5251	Approved
0.5656	Remote Similarity	NPD5248	Approved
0.5656	Remote Similarity	NPD5250	Approved
0.5656	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD5169	Approved
0.5649	Remote Similarity	NPD7507	Approved
0.5648	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7637	Suspended
0.5625	Remote Similarity	NPD6059	Approved
0.562	Remote Similarity	NPD5128	Approved
0.5615	Remote Similarity	NPD7604	Phase 2
0.5614	Remote Similarity	NPD4629	Approved
0.5614	Remote Similarity	NPD5210	Approved
0.561	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.561	Remote Similarity	NPD5216	Approved
0.561	Remote Similarity	NPD5215	Approved
0.561	Remote Similarity	NPD5217	Approved
0.561	Remote Similarity	NPD5127	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