NPASS Compound

Structure

NPC174273 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 5.6379 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1027 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 -3.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5352 -0.7569 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 3.3559 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 0.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -2.3090 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 4.8948 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 -1.5000 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 -0.0000 -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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 14 15 1 0 0 0 0 15 13 1 1 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 19 1 1 0 0 0 17 21 1 0 0 0 0 18 20 1 1 0 0 0 18 22 1 0 0 0 0 19 4 1 1 0 0 0 20 5 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.17
Volume:	368.954
LogP:	4.746
LogD:	3.758
LogS:	-4.297
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.501
Synthetic Accessibility Score:	5.364
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.316
MDCK Permeability:	3.173675941070542e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.157
30% Bioavailability (F30%):	0.84

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.835
Plasma Protein Binding (PPB):	94.81768035888672%
Volume Distribution (VD):	1.118
Pgp-substrate:	4.039270877838135%

ADMET: Metabolism

CYP1A2-inhibitor:	0.159
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.117
CYP2C19-substrate:	0.72
CYP2C9-inhibitor:	0.43
CYP2C9-substrate:	0.226
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.528
CYP3A4-inhibitor:	0.507
CYP3A4-substrate:	0.489

ADMET: Excretion

Clearance (CL):	5.888
Half-life (T1/2):	0.076

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.771
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.329
Carcinogencity:	0.793
Eye Corrosion:	0.057
Eye Irritation:	0.051
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC174273

Natural Product ID:	NPC174273
*Common Name:**	10R-Hydroxybromocorodienol
IUPAC Name:	(1S,2R,4S,4aS,8S,11E,12aS)-4-bromo-1,4a-dimethyl-7-methylidene-8-propan-2-yl-3,4,5,6,8,9,10,12a-octahydro-2H-benzo[10]annulene-1,2-diol
Synonyms:	10R-Hydroxybromocorodienol
Standard InCHIKey:	OSFHGDFNIHPDBE-WPLOQTPPSA-N
Standard InCHI:	InChI=1S/C20H33BrO2/c1-13(2)15-8-6-7-9-16-19(4,11-10-14(15)3)17(21)12-18(22)20(16,5)23/h7,9,13,15-18,22-23H,3,6,8,10-12H2,1-2,4-5H3/b9-7+/t15-,16-,17-,18+,19-,20-/m0/s1
SMILES:	CC([C@@H]1CC/C=C/[C@H]2[C@@](CCC1=C)(C)[C@@H](Br)C[C@H]([C@@]2(C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL599325
PubChem CID:	46232273
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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	=	64000.0	nM	PMID[467961]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	62000.0	nM	PMID[467961]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	48000.0	nM	PMID[467961]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	24000.0	nM	PMID[467961]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	60000.0	nM	PMID[467961]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	33000.0	nM	PMID[467961]

☑ 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 NPC174273 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	205
0.1-0.2	1906
0.2-0.3	8412
0.3-0.4	17541
0.4-0.5	8891
0.5-0.6	4912
0.6-0.7	744
0.7-0.8	77
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8851	High Similarity	NPC239453
0.8851	High Similarity	NPC224552
0.8571	High Similarity	NPC299714
0.8571	High Similarity	NPC257510
0.8391	Intermediate Similarity	NPC313115
0.828	Intermediate Similarity	NPC156912
0.8191	Intermediate Similarity	NPC92231
0.8191	Intermediate Similarity	NPC34732
0.8118	Intermediate Similarity	NPC476610
0.8111	Intermediate Similarity	NPC188896
0.8072	Intermediate Similarity	NPC476605
0.7912	Intermediate Similarity	NPC131453
0.7831	Intermediate Similarity	NPC476609
0.7816	Intermediate Similarity	NPC113024
0.7765	Intermediate Similarity	NPC476606
0.7727	Intermediate Similarity	NPC311891
0.7701	Intermediate Similarity	NPC129501
0.7647	Intermediate Similarity	NPC35397
0.7647	Intermediate Similarity	NPC477923
0.7647	Intermediate Similarity	NPC474946
0.7647	Intermediate Similarity	NPC66566
0.7614	Intermediate Similarity	NPC287749
0.7586	Intermediate Similarity	NPC274750
0.7586	Intermediate Similarity	NPC215307
0.7558	Intermediate Similarity	NPC61080
0.7558	Intermediate Similarity	NPC265588
0.7529	Intermediate Similarity	NPC243342
0.7529	Intermediate Similarity	NPC477138
0.7525	Intermediate Similarity	NPC133921
0.75	Intermediate Similarity	NPC242992
0.75	Intermediate Similarity	NPC471268
0.75	Intermediate Similarity	NPC471271
0.75	Intermediate Similarity	NPC167706
0.7471	Intermediate Similarity	NPC477924
0.7442	Intermediate Similarity	NPC291503
0.7356	Intermediate Similarity	NPC476607
0.7356	Intermediate Similarity	NPC274079
0.7356	Intermediate Similarity	NPC477925
0.7333	Intermediate Similarity	NPC474531
0.7326	Intermediate Similarity	NPC91858
0.7317	Intermediate Similarity	NPC250977
0.7303	Intermediate Similarity	NPC476603
0.7294	Intermediate Similarity	NPC475077
0.7294	Intermediate Similarity	NPC242001
0.7284	Intermediate Similarity	NPC225415
0.7273	Intermediate Similarity	NPC471798
0.7262	Intermediate Similarity	NPC476604
0.7222	Intermediate Similarity	NPC236112
0.7222	Intermediate Similarity	NPC13554
0.7209	Intermediate Similarity	NPC471799
0.7209	Intermediate Similarity	NPC68443
0.7209	Intermediate Similarity	NPC182717
0.7191	Intermediate Similarity	NPC83351
0.7191	Intermediate Similarity	NPC167891
0.7176	Intermediate Similarity	NPC145498
0.7176	Intermediate Similarity	NPC92801
0.7174	Intermediate Similarity	NPC207013
0.7159	Intermediate Similarity	NPC167873
0.7159	Intermediate Similarity	NPC1973
0.7143	Intermediate Similarity	NPC471270
0.7143	Intermediate Similarity	NPC208999
0.7143	Intermediate Similarity	NPC244790
0.7128	Intermediate Similarity	NPC94462
0.7126	Intermediate Similarity	NPC201048
0.7126	Intermediate Similarity	NPC471797
0.7126	Intermediate Similarity	NPC476366
0.7111	Intermediate Similarity	NPC291379
0.7111	Intermediate Similarity	NPC328714
0.7111	Intermediate Similarity	NPC31330
0.7097	Intermediate Similarity	NPC238992
0.7093	Intermediate Similarity	NPC110799
0.7093	Intermediate Similarity	NPC471272
0.7093	Intermediate Similarity	NPC164022
0.7093	Intermediate Similarity	NPC477792
0.7079	Intermediate Similarity	NPC470711
0.7079	Intermediate Similarity	NPC130136
0.7079	Intermediate Similarity	NPC91594
0.7079	Intermediate Similarity	NPC470758
0.7073	Intermediate Similarity	NPC290367
0.7065	Intermediate Similarity	NPC47763
0.7065	Intermediate Similarity	NPC471408
0.7065	Intermediate Similarity	NPC30166
0.7059	Intermediate Similarity	NPC9942
0.7053	Intermediate Similarity	NPC109900
0.7033	Intermediate Similarity	NPC471266
0.7033	Intermediate Similarity	NPC22403
0.7033	Intermediate Similarity	NPC96362
0.7033	Intermediate Similarity	NPC474592
0.7033	Intermediate Similarity	NPC95124
0.7033	Intermediate Similarity	NPC236707
0.7021	Intermediate Similarity	NPC290731
0.7011	Intermediate Similarity	NPC95165
0.7	Intermediate Similarity	NPC474989
0.7	Intermediate Similarity	NPC285761
0.7	Intermediate Similarity	NPC470396
0.7	Intermediate Similarity	NPC99168
0.7	Intermediate Similarity	NPC275910
0.7	Intermediate Similarity	NPC22955
0.6989	Remote Similarity	NPC317458
0.6989	Remote Similarity	NPC159168
0.6989	Remote Similarity	NPC253402
0.6979	Remote Similarity	NPC133588
0.6966	Remote Similarity	NPC106432
0.6966	Remote Similarity	NPC315261
0.6966	Remote Similarity	NPC470749
0.6957	Remote Similarity	NPC476646
0.6957	Remote Similarity	NPC142163
0.6957	Remote Similarity	NPC6707
0.6957	Remote Similarity	NPC249423
0.6947	Remote Similarity	NPC237344
0.6947	Remote Similarity	NPC475069
0.6947	Remote Similarity	NPC175145
0.6941	Remote Similarity	NPC471238
0.6932	Remote Similarity	NPC78527
0.6932	Remote Similarity	NPC100334
0.6932	Remote Similarity	NPC306727
0.6932	Remote Similarity	NPC237510
0.6932	Remote Similarity	NPC475793
0.6923	Remote Similarity	NPC273410
0.6923	Remote Similarity	NPC472463
0.6923	Remote Similarity	NPC233295
0.6923	Remote Similarity	NPC80530
0.6923	Remote Similarity	NPC53744
0.6915	Remote Similarity	NPC474493
0.6907	Remote Similarity	NPC115607
0.6907	Remote Similarity	NPC97103
0.6907	Remote Similarity	NPC329643
0.6889	Remote Similarity	NPC157996
0.6889	Remote Similarity	NPC101475
0.6889	Remote Similarity	NPC472805
0.6889	Remote Similarity	NPC283619
0.6889	Remote Similarity	NPC198968
0.6889	Remote Similarity	NPC155986
0.6889	Remote Similarity	NPC34177
0.6889	Remote Similarity	NPC318495
0.6889	Remote Similarity	NPC90979
0.6889	Remote Similarity	NPC40394
0.6889	Remote Similarity	NPC214570
0.6882	Remote Similarity	NPC49964
0.6882	Remote Similarity	NPC87489
0.6882	Remote Similarity	NPC296701
0.6882	Remote Similarity	NPC7988
0.6882	Remote Similarity	NPC218616
0.6875	Remote Similarity	NPC476948
0.6867	Remote Similarity	NPC144650
0.686	Remote Similarity	NPC476431
0.686	Remote Similarity	NPC210323
0.6854	Remote Similarity	NPC32832
0.6848	Remote Similarity	NPC164840
0.6848	Remote Similarity	NPC241290
0.6848	Remote Similarity	NPC15714
0.6848	Remote Similarity	NPC209944
0.6848	Remote Similarity	NPC236237
0.6848	Remote Similarity	NPC322313
0.6848	Remote Similarity	NPC102253
0.6837	Remote Similarity	NPC204188
0.6837	Remote Similarity	NPC475751
0.6837	Remote Similarity	NPC329596
0.6837	Remote Similarity	NPC291484
0.6837	Remote Similarity	NPC80561
0.6837	Remote Similarity	NPC3345
0.6837	Remote Similarity	NPC11216
0.6837	Remote Similarity	NPC473956
0.6818	Remote Similarity	NPC476422
0.6818	Remote Similarity	NPC220939
0.6818	Remote Similarity	NPC265485
0.6813	Remote Similarity	NPC148977
0.6813	Remote Similarity	NPC244385
0.6813	Remote Similarity	NPC230295
0.6813	Remote Similarity	NPC300499
0.6813	Remote Similarity	NPC11908
0.6813	Remote Similarity	NPC476314
0.6813	Remote Similarity	NPC138621
0.6813	Remote Similarity	NPC158662
0.6813	Remote Similarity	NPC196753
0.6813	Remote Similarity	NPC253807
0.6813	Remote Similarity	NPC167037
0.6813	Remote Similarity	NPC6978
0.6813	Remote Similarity	NPC98386
0.6809	Remote Similarity	NPC82538
0.6809	Remote Similarity	NPC237795
0.6809	Remote Similarity	NPC185605
0.6809	Remote Similarity	NPC474634
0.6809	Remote Similarity	NPC23748
0.6804	Remote Similarity	NPC475664
0.6804	Remote Similarity	NPC474668
0.6782	Remote Similarity	NPC34834
0.6778	Remote Similarity	NPC265328
0.6778	Remote Similarity	NPC237460
0.6778	Remote Similarity	NPC113733
0.6778	Remote Similarity	NPC129165
0.6778	Remote Similarity	NPC63958
0.6778	Remote Similarity	NPC300324
0.6778	Remote Similarity	NPC134330
0.6778	Remote Similarity	NPC73875
0.6778	Remote Similarity	NPC321016
0.6778	Remote Similarity	NPC107059
0.6778	Remote Similarity	NPC470362
0.6778	Remote Similarity	NPC321381
0.6778	Remote Similarity	NPC120098

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 NPC174273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	2453
0.2-0.3	4184
0.3-0.4	1771
0.4-0.5	353
0.5-0.6	165
0.6-0.7	18
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
0.6966	Remote Similarity	NPD6933	Approved
0.6848	Remote Similarity	NPD7525	Registered
0.6742	Remote Similarity	NPD6926	Approved
0.6742	Remote Similarity	NPD6924	Approved
0.6739	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD8264	Approved
0.6593	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7150	Approved
0.6517	Remote Similarity	NPD7151	Approved
0.6517	Remote Similarity	NPD7152	Approved
0.6489	Remote Similarity	NPD7509	Discontinued
0.6404	Remote Similarity	NPD7143	Approved
0.6404	Remote Similarity	NPD7144	Approved
0.6364	Remote Similarity	NPD7524	Approved
0.6344	Remote Similarity	NPD6932	Approved
0.6316	Remote Similarity	NPD6931	Approved
0.6316	Remote Similarity	NPD6930	Phase 2
0.6292	Remote Similarity	NPD6922	Approved
0.6292	Remote Similarity	NPD6923	Approved
0.6277	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4786	Approved
0.6211	Remote Similarity	NPD6929	Approved
0.6196	Remote Similarity	NPD4784	Approved
0.6196	Remote Similarity	NPD4785	Approved
0.6186	Remote Similarity	NPD3667	Approved
0.6146	Remote Similarity	NPD4748	Discontinued
0.6146	Remote Similarity	NPD7332	Phase 2
0.6146	Remote Similarity	NPD7514	Phase 3
0.6122	Remote Similarity	NPD6695	Phase 3
0.6117	Remote Similarity	NPD6079	Approved
0.6105	Remote Similarity	NPD7145	Approved
0.61	Remote Similarity	NPD3618	Phase 1
0.6078	Remote Similarity	NPD5328	Approved
0.6061	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6683	Phase 2
0.604	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6925	Approved
0.6	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD5776	Phase 2
0.5978	Remote Similarity	NPD4243	Approved
0.5963	Remote Similarity	NPD5344	Discontinued
0.5962	Remote Similarity	NPD7515	Phase 2
0.5926	Remote Similarity	NPD4225	Approved
0.5918	Remote Similarity	NPD6902	Approved
0.5918	Remote Similarity	NPD6898	Phase 1
0.5905	Remote Similarity	NPD4202	Approved
0.5882	Remote Similarity	NPD7750	Discontinued
0.5862	Remote Similarity	NPD368	Approved
0.5766	Remote Similarity	NPD7632	Discontinued
0.5761	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD3666	Approved
0.5743	Remote Similarity	NPD3665	Phase 1
0.5743	Remote Similarity	NPD3133	Approved
0.5741	Remote Similarity	NPD5222	Approved
0.5741	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5221	Approved
0.5727	Remote Similarity	NPD5286	Approved
0.5727	Remote Similarity	NPD5285	Approved
0.5727	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD4195	Approved
0.5714	Remote Similarity	NPD3168	Discontinued
0.5701	Remote Similarity	NPD7748	Approved
0.5688	Remote Similarity	NPD5173	Approved
0.5688	Remote Similarity	NPD4755	Approved
0.5686	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD4159	Approved
0.5676	Remote Similarity	NPD5223	Approved
0.566	Remote Similarity	NPD6411	Approved
0.566	Remote Similarity	NPD7087	Discontinued
0.5657	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD5290	Discontinued
0.5636	Remote Similarity	NPD7638	Approved
0.5631	Remote Similarity	NPD5279	Phase 3
0.5625	Remote Similarity	NPD5224	Approved
0.5625	Remote Similarity	NPD4190	Phase 3
0.5625	Remote Similarity	NPD5225	Approved
0.5625	Remote Similarity	NPD5275	Approved
0.5625	Remote Similarity	NPD4633	Approved
0.5625	Remote Similarity	NPD5226	Approved
0.5625	Remote Similarity	NPD5211	Phase 2
0.5607	Remote Similarity	NPD6399	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