NPASS Compound

Structure

NPC84426 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 -2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 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 0.8660 0.5000 0.0000 C 0 0 0 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 0.0000 -3.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 7 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 18 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 7 1 1 0 0 0 9 12 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 1 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 18 1 0 0 0 0 17 23 2 0 0 0 0 18 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	441.98
Volume:	345.97
LogP:	5.489
LogD:	3.717
LogS:	-6.381
# Rotatable Bonds:	1
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.61
Synthetic Accessibility Score:	4.242
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.608
MDCK Permeability:	1.684065136942081e-05
Pgp-inhibitor:	0.309
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.238
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	101.26696014404297%
Volume Distribution (VD):	1.133
Pgp-substrate:	1.5323225259780884%

ADMET: Metabolism

CYP1A2-inhibitor:	0.407
CYP1A2-substrate:	0.913
CYP2C19-inhibitor:	0.614
CYP2C19-substrate:	0.822
CYP2C9-inhibitor:	0.92
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.263
CYP3A4-inhibitor:	0.32
CYP3A4-substrate:	0.466

ADMET: Excretion

Clearance (CL):	0.936
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.575
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.626
Maximum Recommended Daily Dose:	0.57
Skin Sensitization:	0.414
Carcinogencity:	0.082
Eye Corrosion:	0.006
Eye Irritation:	0.825
Respiratory Toxicity:	0.373

Download Data

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

Natural Product: NPC84426

Natural Product ID:	NPC84426
*Common Name:**	4-Bromohamigeran B
IUPAC Name:	(1R,3aR,9bS)-7,9-dibromo-6-hydroxy-3a,8-dimethyl-1-propan-2-yl-1,2,3,9b-tetrahydrocyclopenta[a]naphthalene-4,5-dione
Synonyms:
Standard InCHIKey:	XKEGJOWTEPEJJA-YHRQMHJJSA-N
Standard InCHI:	InChI=1S/C18H20Br2O3/c1-7(2)9-5-6-18(4)12(9)10-11(16(22)17(18)23)15(21)14(20)8(3)13(10)19/h7,9,12,21H,5-6H2,1-4H3/t9-,12-,18-/m1/s1
SMILES:	CC(C)[C@H]1CC[C@]2(C)[C@H]1c1c(c(c(c(C)c1Br)Br)O)C(=O)C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519430
PubChem CID:	10478608
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO2050	Hamigera tarangaensis	Species	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650083]
NPO2050	Hamigera tarangaensis	Species	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29373034]
NPO2050	Hamigera tarangaensis	Species	Hymedesmiidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	13900.0	nM	PMID[500160]

☑ 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 NPC84426 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	428
0.1-0.2	2152
0.2-0.3	5020
0.3-0.4	14844
0.4-0.5	10928
0.5-0.6	8265
0.6-0.7	1037
0.7-0.8	18
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC160839
0.8176	Intermediate Similarity	NPC200331
0.8086	Intermediate Similarity	NPC293312
0.7593	Intermediate Similarity	NPC474777
0.7485	Intermediate Similarity	NPC203426
0.7483	Intermediate Similarity	NPC19432
0.7397	Intermediate Similarity	NPC12818
0.7361	Intermediate Similarity	NPC472046
0.731	Intermediate Similarity	NPC24435
0.7248	Intermediate Similarity	NPC471530
0.72	Intermediate Similarity	NPC48248
0.7193	Intermediate Similarity	NPC470566
0.7181	Intermediate Similarity	NPC472047
0.7171	Intermediate Similarity	NPC17083
0.7162	Intermediate Similarity	NPC68756
0.7162	Intermediate Similarity	NPC142956
0.7162	Intermediate Similarity	NPC152525
0.7161	Intermediate Similarity	NPC472308
0.7161	Intermediate Similarity	NPC193358
0.7152	Intermediate Similarity	NPC105702
0.7151	Intermediate Similarity	NPC470567
0.7143	Intermediate Similarity	NPC307174
0.7143	Intermediate Similarity	NPC52368
0.7143	Intermediate Similarity	NPC218854
0.7133	Intermediate Similarity	NPC84672
0.7133	Intermediate Similarity	NPC72667
0.7133	Intermediate Similarity	NPC176130
0.7133	Intermediate Similarity	NPC78364
0.7133	Intermediate Similarity	NPC69424
0.7124	Intermediate Similarity	NPC58685
0.7118	Intermediate Similarity	NPC471687
0.7105	Intermediate Similarity	NPC108129
0.7095	Intermediate Similarity	NPC275145
0.7078	Intermediate Similarity	NPC115458
0.7078	Intermediate Similarity	NPC114183
0.7075	Intermediate Similarity	NPC154696
0.7067	Intermediate Similarity	NPC254492
0.7051	Intermediate Similarity	NPC474311
0.7047	Intermediate Similarity	NPC173978
0.7047	Intermediate Similarity	NPC74507
0.7047	Intermediate Similarity	NPC199273
0.7047	Intermediate Similarity	NPC234890
0.7039	Intermediate Similarity	NPC146647
0.7039	Intermediate Similarity	NPC34414
0.7039	Intermediate Similarity	NPC171460
0.7039	Intermediate Similarity	NPC303910
0.7039	Intermediate Similarity	NPC276238
0.7032	Intermediate Similarity	NPC270899
0.7032	Intermediate Similarity	NPC12070
0.7014	Intermediate Similarity	NPC477453
0.7	Intermediate Similarity	NPC131799
0.6993	Remote Similarity	NPC475741
0.6993	Remote Similarity	NPC55949
0.6987	Remote Similarity	NPC249272
0.6974	Remote Similarity	NPC282923
0.6974	Remote Similarity	NPC3009
0.6968	Remote Similarity	NPC111845
0.6968	Remote Similarity	NPC138472
0.6954	Remote Similarity	NPC227741
0.6954	Remote Similarity	NPC136342
0.6954	Remote Similarity	NPC49647
0.6954	Remote Similarity	NPC295202
0.6954	Remote Similarity	NPC306765
0.6954	Remote Similarity	NPC71610
0.6954	Remote Similarity	NPC3224
0.6954	Remote Similarity	NPC160499
0.6948	Remote Similarity	NPC471851
0.6943	Remote Similarity	NPC272268
0.6939	Remote Similarity	NPC206778
0.6939	Remote Similarity	NPC285829
0.6937	Remote Similarity	NPC477275
0.6937	Remote Similarity	NPC92079
0.6923	Remote Similarity	NPC161964
0.6923	Remote Similarity	NPC202225
0.6923	Remote Similarity	NPC472262
0.6923	Remote Similarity	NPC287604
0.6913	Remote Similarity	NPC282577
0.6913	Remote Similarity	NPC300274
0.6899	Remote Similarity	NPC53001
0.6892	Remote Similarity	NPC259703
0.6892	Remote Similarity	NPC190971
0.6892	Remote Similarity	NPC32322
0.6879	Remote Similarity	NPC153088
0.6879	Remote Similarity	NPC283088
0.6879	Remote Similarity	NPC90245
0.6875	Remote Similarity	NPC96421
0.6871	Remote Similarity	NPC473974
0.6871	Remote Similarity	NPC79933
0.6871	Remote Similarity	NPC258366
0.6871	Remote Similarity	NPC31296
0.6867	Remote Similarity	NPC375356
0.6867	Remote Similarity	NPC198014
0.6863	Remote Similarity	NPC96024
0.6859	Remote Similarity	NPC225051
0.6859	Remote Similarity	NPC53896
0.6859	Remote Similarity	NPC78307
0.6859	Remote Similarity	NPC477139
0.6857	Remote Similarity	NPC475976
0.6855	Remote Similarity	NPC87723
0.6839	Remote Similarity	NPC205992
0.6839	Remote Similarity	NPC72669
0.6839	Remote Similarity	NPC244699
0.6839	Remote Similarity	NPC474517
0.6839	Remote Similarity	NPC41847
0.6839	Remote Similarity	NPC85342
0.6835	Remote Similarity	NPC471237
0.6835	Remote Similarity	NPC177967
0.6828	Remote Similarity	NPC161304
0.6824	Remote Similarity	NPC318552
0.6824	Remote Similarity	NPC190501
0.6821	Remote Similarity	NPC181334
0.6821	Remote Similarity	NPC236189
0.6818	Remote Similarity	NPC99731
0.6818	Remote Similarity	NPC25736
0.6818	Remote Similarity	NPC278928
0.6815	Remote Similarity	NPC50924
0.68	Remote Similarity	NPC176208
0.6792	Remote Similarity	NPC475957
0.6792	Remote Similarity	NPC36868
0.6792	Remote Similarity	NPC471236
0.6792	Remote Similarity	NPC197766
0.6792	Remote Similarity	NPC245923
0.6779	Remote Similarity	NPC241001
0.6776	Remote Similarity	NPC103540
0.6776	Remote Similarity	NPC123506
0.6774	Remote Similarity	NPC31799
0.6774	Remote Similarity	NPC198305
0.6774	Remote Similarity	NPC136588
0.6774	Remote Similarity	NPC199253
0.6772	Remote Similarity	NPC80035
0.6772	Remote Similarity	NPC477596
0.677	Remote Similarity	NPC181560
0.677	Remote Similarity	NPC169452
0.6765	Remote Similarity	NPC25850
0.6765	Remote Similarity	NPC276815
0.6755	Remote Similarity	NPC471187
0.6752	Remote Similarity	NPC314048
0.675	Remote Similarity	NPC230811
0.6748	Remote Similarity	NPC199936
0.6733	Remote Similarity	NPC162935
0.6733	Remote Similarity	NPC249340
0.6732	Remote Similarity	NPC231774
0.6732	Remote Similarity	NPC96915
0.673	Remote Similarity	NPC474813
0.673	Remote Similarity	NPC155211
0.673	Remote Similarity	NPC191976
0.6728	Remote Similarity	NPC106519
0.6728	Remote Similarity	NPC91019
0.6727	Remote Similarity	NPC143685
0.6725	Remote Similarity	NPC283301
0.6712	Remote Similarity	NPC469719
0.6711	Remote Similarity	NPC310540
0.6711	Remote Similarity	NPC473662
0.6711	Remote Similarity	NPC7151
0.6711	Remote Similarity	NPC216297
0.671	Remote Similarity	NPC131684
0.6709	Remote Similarity	NPC474117
0.6709	Remote Similarity	NPC474224
0.6709	Remote Similarity	NPC166480
0.6709	Remote Similarity	NPC477594
0.6709	Remote Similarity	NPC282780
0.6708	Remote Similarity	NPC138099
0.6708	Remote Similarity	NPC242994
0.6689	Remote Similarity	NPC121168
0.6689	Remote Similarity	NPC244351
0.6689	Remote Similarity	NPC11250
0.6688	Remote Similarity	NPC309430
0.6688	Remote Similarity	NPC88864
0.6688	Remote Similarity	NPC110609
0.6688	Remote Similarity	NPC474109
0.6688	Remote Similarity	NPC242358
0.6688	Remote Similarity	NPC70622
0.6688	Remote Similarity	NPC246693
0.6687	Remote Similarity	NPC49911
0.6687	Remote Similarity	NPC305060
0.6687	Remote Similarity	NPC471905
0.6687	Remote Similarity	NPC193555
0.6687	Remote Similarity	NPC277559
0.6687	Remote Similarity	NPC477209
0.6686	Remote Similarity	NPC471541
0.6667	Remote Similarity	NPC225243
0.6667	Remote Similarity	NPC137750
0.6667	Remote Similarity	NPC31539
0.6667	Remote Similarity	NPC159760
0.6667	Remote Similarity	NPC471853
0.6667	Remote Similarity	NPC272454
0.6667	Remote Similarity	NPC35856
0.6667	Remote Similarity	NPC87985
0.6667	Remote Similarity	NPC179092
0.6667	Remote Similarity	NPC301987
0.6667	Remote Similarity	NPC178395
0.6667	Remote Similarity	NPC315578
0.6667	Remote Similarity	NPC474175
0.6667	Remote Similarity	NPC161632
0.6667	Remote Similarity	NPC222876
0.6667	Remote Similarity	NPC26433
0.6667	Remote Similarity	NPC290803
0.6667	Remote Similarity	NPC258502
0.6667	Remote Similarity	NPC115188
0.6667	Remote Similarity	NPC292665

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 NPC84426 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	1226
0.2-0.3	2331
0.3-0.4	3356
0.4-0.5	1471
0.5-0.6	340
0.6-0.7	25
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
0.6905	Remote Similarity	NPD2296	Approved
0.6846	Remote Similarity	NPD1201	Approved
0.6824	Remote Similarity	NPD2932	Approved
0.6824	Remote Similarity	NPD3019	Approved
0.6776	Remote Similarity	NPD1470	Approved
0.6667	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD9244	Approved
0.6481	Remote Similarity	NPD5404	Approved
0.6481	Remote Similarity	NPD5406	Approved
0.6481	Remote Similarity	NPD5408	Approved
0.6481	Remote Similarity	NPD5405	Approved
0.6467	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD2346	Discontinued
0.6424	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD7390	Discontinued
0.6398	Remote Similarity	NPD4287	Approved
0.634	Remote Similarity	NPD3026	Approved
0.634	Remote Similarity	NPD3023	Approved
0.6316	Remote Similarity	NPD3024	Approved
0.6316	Remote Similarity	NPD3025	Approved
0.6272	Remote Similarity	NPD2532	Approved
0.6272	Remote Similarity	NPD2534	Approved
0.6272	Remote Similarity	NPD2533	Approved
0.625	Remote Similarity	NPD3300	Phase 2
0.6229	Remote Similarity	NPD4288	Approved
0.6211	Remote Similarity	NPD6663	Approved
0.62	Remote Similarity	NPD5951	Approved
0.6196	Remote Similarity	NPD6651	Approved
0.6174	Remote Similarity	NPD7635	Approved
0.6169	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD2800	Approved
0.6164	Remote Similarity	NPD5736	Approved
0.6158	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD1164	Approved
0.6136	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD7003	Approved
0.6127	Remote Similarity	NPD3226	Approved
0.6121	Remote Similarity	NPD2799	Discontinued
0.6101	Remote Similarity	NPD2798	Approved
0.6084	Remote Similarity	NPD2935	Discontinued
0.6065	Remote Similarity	NPD4059	Approved
0.6039	Remote Similarity	NPD3091	Approved
0.6024	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD1161	Approved
0.5976	Remote Similarity	NPD943	Approved
0.5975	Remote Similarity	NPD1876	Approved
0.5974	Remote Similarity	NPD7610	Discontinued
0.5962	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD6273	Approved
0.5952	Remote Similarity	NPD2344	Approved
0.5951	Remote Similarity	NPD2313	Discontinued
0.5946	Remote Similarity	NPD2342	Discontinued
0.5924	Remote Similarity	NPD7473	Discontinued
0.5909	Remote Similarity	NPD7340	Approved
0.5893	Remote Similarity	NPD6100	Approved
0.5893	Remote Similarity	NPD6099	Approved
0.589	Remote Similarity	NPD9718	Approved
0.5886	Remote Similarity	NPD3092	Approved
0.5879	Remote Similarity	NPD6959	Discontinued
0.5875	Remote Similarity	NPD1283	Approved
0.5854	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD5711	Approved
0.5847	Remote Similarity	NPD5710	Approved
0.5847	Remote Similarity	NPD6232	Discontinued
0.5833	Remote Similarity	NPD651	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7009	Phase 2
0.5824	Remote Similarity	NPD970	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD8032	Phase 2
0.5817	Remote Similarity	NPD1398	Phase 1
0.5814	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD2309	Approved
0.5808	Remote Similarity	NPD1607	Approved
0.5806	Remote Similarity	NPD9493	Approved
0.58	Remote Similarity	NPD9266	Approved
0.58	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.58	Remote Similarity	NPD74	Approved
0.5796	Remote Similarity	NPD1651	Approved
0.5793	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD4445	Approved
0.5769	Remote Similarity	NPD1168	Approved
0.5765	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD288	Approved
0.5763	Remote Similarity	NPD7458	Discontinued
0.5763	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD4750	Phase 3
0.5759	Remote Similarity	NPD4626	Approved
0.5759	Remote Similarity	NPD3095	Discontinued
0.5758	Remote Similarity	NPD3764	Approved
0.5756	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.5756	Remote Similarity	NPD8166	Discontinued
0.575	Remote Similarity	NPD3972	Approved
0.5741	Remote Similarity	NPD3094	Phase 2
0.5733	Remote Similarity	NPD9263	Approved
0.5733	Remote Similarity	NPD9264	Approved
0.5733	Remote Similarity	NPD9267	Approved
0.5722	Remote Similarity	NPD7819	Suspended
0.5714	Remote Similarity	NPD1755	Approved
0.5714	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.5697	Remote Similarity	NPD7008	Discontinued
0.5694	Remote Similarity	NPD1809	Phase 2
0.5694	Remote Similarity	NPD844	Approved
0.5689	Remote Similarity	NPD1240	Approved
0.5687	Remote Similarity	NPD1281	Approved
0.5679	Remote Similarity	NPD6696	Suspended
0.5676	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD1929	Approved
0.5676	Remote Similarity	NPD1930	Approved
0.5673	Remote Similarity	NPD1471	Phase 3
0.5664	Remote Similarity	NPD845	Approved
0.5652	Remote Similarity	NPD4878	Approved
0.5646	Remote Similarity	NPD289	Clinical (unspecified phase)
0.5642	Remote Similarity	NPD7028	Phase 2
0.5635	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8313	Approved
0.5625	Remote Similarity	NPD8312	Approved
0.5625	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.5621	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD8150	Discontinued
0.561	Remote Similarity	NPD4624	Approved
0.5608	Remote Similarity	NPD6020	Phase 2
0.5605	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.5602	Remote Similarity	NPD5027	Approved
0.5602	Remote Similarity	NPD5029	Approved
0.5602	Remote Similarity	NPD5031	Approved
0.56	Remote Similarity	NPD7236	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