NPASS Compound

Structure

NPC160839 OpenBabel07101718202D 22 24 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 -0.8660 2.5000 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 -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 -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 8 1 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 18 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 9 14 1 0 0 0 0 10 8 1 1 0 0 0 10 13 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 18 1 1 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.07
Volume:	326.687
LogP:	4.644
LogD:	3.48
LogS:	-5.556
# Rotatable Bonds:	1
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.752
Synthetic Accessibility Score:	4.116
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:	-4.664
MDCK Permeability:	1.8857665054383688e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	100.66585540771484%
Volume Distribution (VD):	0.531
Pgp-substrate:	1.508467435836792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.648
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.722
CYP2C19-substrate:	0.776
CYP2C9-inhibitor:	0.867
CYP2C9-substrate:	0.847
CYP2D6-inhibitor:	0.298
CYP2D6-substrate:	0.361
CYP3A4-inhibitor:	0.461
CYP3A4-substrate:	0.416

ADMET: Excretion

Clearance (CL):	0.966
Half-life (T1/2):	0.055

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.411
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.499
Maximum Recommended Daily Dose:	0.506
Skin Sensitization:	0.348
Carcinogencity:	0.185
Eye Corrosion:	0.003
Eye Irritation:	0.557
Respiratory Toxicity:	0.721

Download Data

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

Natural Product: NPC160839

Natural Product ID:	NPC160839
*Common Name:**	Hamigeran B
IUPAC Name:	(1R,3aR,9bR)-7-bromo-6-hydroxy-3a,8-dimethyl-1-propan-2-yl-1,2,3,9b-tetrahydrocyclopenta[a]naphthalene-4,5-dione
Synonyms:
Standard InCHIKey:	LJUSWSWJFIZLDY-AJAPIDPKSA-N
Standard InCHI:	InChI=1S/C18H21BrO3/c1-8(2)10-5-6-18(4)13(10)11-7-9(3)14(19)15(20)12(11)16(21)17(18)22/h7-8,10,13,20H,5-6H2,1-4H3/t10-,13-,18-/m1/s1
SMILES:	CC([C@H]1CC[C@@]2([C@H]1c1cc(C)c(c(c1C(=O)C2=O)O)Br)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL380587
PubChem CID:	9976066
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	3
Others	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	13500.0	nM	PMID[477072]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13500.0	nM	PMID[477070]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13500.0	nM	PMID[477071]
NPT2665	Organism	unidentified herpesvirus	unidentified herpesvirus	Inhibition	=	100.0	%	PMID[477072]
NPT1048	Organism	Poliovirus	Human enterovirus C	Inhibition	=	100.0	%	PMID[477072]

☑ 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 NPC160839 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	407
0.1-0.2	1837
0.2-0.3	3878
0.3-0.4	12593
0.4-0.5	10198
0.5-0.6	10695
0.6-0.7	2850
0.7-0.8	233
0.8-0.85	1
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC84426
0.8766	High Similarity	NPC200331
0.8662	High Similarity	NPC293312
0.8153	Intermediate Similarity	NPC474777
0.7793	Intermediate Similarity	NPC48248
0.7762	Intermediate Similarity	NPC68756
0.7762	Intermediate Similarity	NPC142956
0.7762	Intermediate Similarity	NPC152525
0.7746	Intermediate Similarity	NPC307174
0.7733	Intermediate Similarity	NPC472308
0.7733	Intermediate Similarity	NPC193358
0.7724	Intermediate Similarity	NPC176130
0.7724	Intermediate Similarity	NPC72667
0.7724	Intermediate Similarity	NPC19432
0.7724	Intermediate Similarity	NPC78364
0.7724	Intermediate Similarity	NPC69424
0.7724	Intermediate Similarity	NPC471530
0.7724	Intermediate Similarity	NPC84672
0.7703	Intermediate Similarity	NPC58685
0.7692	Intermediate Similarity	NPC275145
0.7687	Intermediate Similarity	NPC108129
0.7676	Intermediate Similarity	NPC154696
0.7655	Intermediate Similarity	NPC254492
0.7651	Intermediate Similarity	NPC114183
0.7651	Intermediate Similarity	NPC115458
0.7639	Intermediate Similarity	NPC234890
0.7639	Intermediate Similarity	NPC173978
0.7639	Intermediate Similarity	NPC199273
0.7639	Intermediate Similarity	NPC74507
0.7635	Intermediate Similarity	NPC17083
0.7626	Intermediate Similarity	NPC477453
0.7619	Intermediate Similarity	NPC24435
0.7619	Intermediate Similarity	NPC146647
0.7619	Intermediate Similarity	NPC276238
0.7619	Intermediate Similarity	NPC171460
0.7619	Intermediate Similarity	NPC34414
0.7605	Intermediate Similarity	NPC470566
0.76	Intermediate Similarity	NPC12070
0.76	Intermediate Similarity	NPC270899
0.7586	Intermediate Similarity	NPC131799
0.7568	Intermediate Similarity	NPC55949
0.7568	Intermediate Similarity	NPC475741
0.756	Intermediate Similarity	NPC470567
0.7551	Intermediate Similarity	NPC282923
0.7551	Intermediate Similarity	NPC3009
0.755	Intermediate Similarity	NPC249272
0.7535	Intermediate Similarity	NPC206778
0.7535	Intermediate Similarity	NPC285829
0.7534	Intermediate Similarity	NPC306765
0.7534	Intermediate Similarity	NPC227741
0.7534	Intermediate Similarity	NPC3224
0.7534	Intermediate Similarity	NPC160499
0.7534	Intermediate Similarity	NPC49647
0.7534	Intermediate Similarity	NPC295202
0.7534	Intermediate Similarity	NPC136342
0.7533	Intermediate Similarity	NPC111845
0.7533	Intermediate Similarity	NPC138472
0.7517	Intermediate Similarity	NPC471851
0.75	Intermediate Similarity	NPC300274
0.75	Intermediate Similarity	NPC474311
0.75	Intermediate Similarity	NPC303910
0.75	Intermediate Similarity	NPC282577
0.75	Intermediate Similarity	NPC272268
0.7484	Intermediate Similarity	NPC477275
0.7483	Intermediate Similarity	NPC190971
0.7483	Intermediate Similarity	NPC287604
0.7483	Intermediate Similarity	NPC259703
0.7483	Intermediate Similarity	NPC32322
0.7483	Intermediate Similarity	NPC202225
0.7483	Intermediate Similarity	NPC161964
0.7483	Intermediate Similarity	NPC472262
0.7465	Intermediate Similarity	NPC79933
0.7465	Intermediate Similarity	NPC258366
0.7465	Intermediate Similarity	NPC473974
0.7465	Intermediate Similarity	NPC31296
0.7451	Intermediate Similarity	NPC53001
0.7448	Intermediate Similarity	NPC375356
0.7434	Intermediate Similarity	NPC283088
0.7434	Intermediate Similarity	NPC153088
0.7432	Intermediate Similarity	NPC96024
0.7429	Intermediate Similarity	NPC161304
0.7419	Intermediate Similarity	NPC96421
0.7417	Intermediate Similarity	NPC477139
0.7417	Intermediate Similarity	NPC225051
0.7417	Intermediate Similarity	NPC78307
0.7417	Intermediate Similarity	NPC53896
0.7415	Intermediate Similarity	NPC71610
0.7413	Intermediate Similarity	NPC318552
0.7413	Intermediate Similarity	NPC190501
0.7403	Intermediate Similarity	NPC87723
0.74	Intermediate Similarity	NPC244699
0.74	Intermediate Similarity	NPC474517
0.74	Intermediate Similarity	NPC41847
0.74	Intermediate Similarity	NPC205992
0.74	Intermediate Similarity	NPC85342
0.74	Intermediate Similarity	NPC72669
0.7397	Intermediate Similarity	NPC236189
0.7397	Intermediate Similarity	NPC12818
0.7397	Intermediate Similarity	NPC181334
0.7383	Intermediate Similarity	NPC278928
0.7383	Intermediate Similarity	NPC99731
0.7383	Intermediate Similarity	NPC25736
0.7381	Intermediate Similarity	NPC90245
0.7381	Intermediate Similarity	NPC203426
0.7379	Intermediate Similarity	NPC176208
0.7368	Intermediate Similarity	NPC50924
0.7368	Intermediate Similarity	NPC52368
0.7368	Intermediate Similarity	NPC218854
0.7361	Intermediate Similarity	NPC472046
0.7361	Intermediate Similarity	NPC241001
0.7353	Intermediate Similarity	NPC475976
0.7347	Intermediate Similarity	NPC123506
0.7347	Intermediate Similarity	NPC103540
0.7338	Intermediate Similarity	NPC245923
0.7338	Intermediate Similarity	NPC36868
0.7338	Intermediate Similarity	NPC475957
0.7333	Intermediate Similarity	NPC199253
0.7333	Intermediate Similarity	NPC136588
0.7333	Intermediate Similarity	NPC198305
0.7333	Intermediate Similarity	NPC31799
0.7329	Intermediate Similarity	NPC471187
0.7329	Intermediate Similarity	NPC198014
0.7321	Intermediate Similarity	NPC471687
0.732	Intermediate Similarity	NPC80035
0.732	Intermediate Similarity	NPC477596
0.731	Intermediate Similarity	NPC249340
0.731	Intermediate Similarity	NPC162935
0.7308	Intermediate Similarity	NPC181560
0.7308	Intermediate Similarity	NPC169452
0.7305	Intermediate Similarity	NPC469719
0.7303	Intermediate Similarity	NPC314048
0.7297	Intermediate Similarity	NPC231774
0.7297	Intermediate Similarity	NPC96915
0.7292	Intermediate Similarity	NPC216297
0.7292	Intermediate Similarity	NPC473662
0.7292	Intermediate Similarity	NPC7151
0.729	Intermediate Similarity	NPC230811
0.7279	Intermediate Similarity	NPC310540
0.7273	Intermediate Similarity	NPC191976
0.7273	Intermediate Similarity	NPC474813
0.7273	Intermediate Similarity	NPC155211
0.7267	Intermediate Similarity	NPC131684
0.7261	Intermediate Similarity	NPC106519
0.7261	Intermediate Similarity	NPC91019
0.726	Intermediate Similarity	NPC244351
0.726	Intermediate Similarity	NPC11250
0.726	Intermediate Similarity	NPC121168
0.7255	Intermediate Similarity	NPC477594
0.7255	Intermediate Similarity	NPC166480
0.7255	Intermediate Similarity	NPC282780
0.7254	Intermediate Similarity	NPC108288
0.725	Intermediate Similarity	NPC143685
0.7244	Intermediate Similarity	NPC138099
0.7244	Intermediate Similarity	NPC242994
0.7241	Intermediate Similarity	NPC26433
0.7241	Intermediate Similarity	NPC178395
0.7241	Intermediate Similarity	NPC244994
0.7241	Intermediate Similarity	NPC474175
0.7241	Intermediate Similarity	NPC301987
0.7241	Intermediate Similarity	NPC35856
0.7241	Intermediate Similarity	NPC115188
0.7241	Intermediate Similarity	NPC272454
0.7241	Intermediate Similarity	NPC222876
0.7241	Intermediate Similarity	NPC159760
0.7241	Intermediate Similarity	NPC179092
0.7241	Intermediate Similarity	NPC292665
0.7237	Intermediate Similarity	NPC70622
0.7237	Intermediate Similarity	NPC309430
0.7237	Intermediate Similarity	NPC246693
0.7237	Intermediate Similarity	NPC242358
0.7237	Intermediate Similarity	NPC110609
0.723	Intermediate Similarity	NPC137750
0.7226	Intermediate Similarity	NPC305060
0.7226	Intermediate Similarity	NPC471905
0.7222	Intermediate Similarity	NPC184579
0.7222	Intermediate Similarity	NPC233165
0.7219	Intermediate Similarity	NPC31539
0.7215	Intermediate Similarity	NPC477209
0.7215	Intermediate Similarity	NPC193555
0.7211	Intermediate Similarity	NPC273683
0.7208	Intermediate Similarity	NPC258502
0.7208	Intermediate Similarity	NPC161632
0.7208	Intermediate Similarity	NPC290803
0.7203	Intermediate Similarity	NPC269414
0.7197	Intermediate Similarity	NPC471853
0.7197	Intermediate Similarity	NPC225243
0.7197	Intermediate Similarity	NPC315578
0.719	Intermediate Similarity	NPC267205
0.719	Intermediate Similarity	NPC52407
0.719	Intermediate Similarity	NPC254603
0.7181	Intermediate Similarity	NPC472047
0.7179	Intermediate Similarity	NPC13715
0.7179	Intermediate Similarity	NPC141368
0.7179	Intermediate Similarity	NPC206207
0.7179	Intermediate Similarity	NPC4214
0.7172	Intermediate Similarity	NPC478121
0.7171	Intermediate Similarity	NPC476847
0.717	Intermediate Similarity	NPC163948
0.717	Intermediate Similarity	NPC199936
0.7162	Intermediate Similarity	NPC15127

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 NPC160839 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	1052
0.2-0.3	1683
0.3-0.4	3317
0.4-0.5	1954
0.5-0.6	681
0.6-0.7	86
0.7-0.8	5
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
0.7431	Intermediate Similarity	NPD1201	Approved
0.7413	Intermediate Similarity	NPD2932	Approved
0.7413	Intermediate Similarity	NPD3019	Approved
0.7347	Intermediate Similarity	NPD1470	Approved
0.7254	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2296	Approved
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.6986	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2346	Discontinued
0.6914	Remote Similarity	NPD7390	Discontinued
0.6892	Remote Similarity	NPD3026	Approved
0.6892	Remote Similarity	NPD3023	Approved
0.6871	Remote Similarity	NPD3025	Approved
0.6871	Remote Similarity	NPD3024	Approved
0.6759	Remote Similarity	NPD5951	Approved
0.6748	Remote Similarity	NPD3300	Phase 2
0.6736	Remote Similarity	NPD7635	Approved
0.6731	Remote Similarity	NPD6663	Approved
0.6688	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD1164	Approved
0.6626	Remote Similarity	NPD7003	Approved
0.6625	Remote Similarity	NPD2799	Discontinued
0.6623	Remote Similarity	NPD2798	Approved
0.6608	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3226	Approved
0.66	Remote Similarity	NPD4059	Approved
0.66	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2935	Discontinued
0.6577	Remote Similarity	NPD3091	Approved
0.6566	Remote Similarity	NPD2532	Approved
0.6566	Remote Similarity	NPD2534	Approved
0.6566	Remote Similarity	NPD2533	Approved
0.6522	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7610	Discontinued
0.6503	Remote Similarity	NPD2342	Discontinued
0.6494	Remote Similarity	NPD1876	Approved
0.649	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD943	Approved
0.6456	Remote Similarity	NPD2313	Discontinued
0.6442	Remote Similarity	NPD2344	Approved
0.6429	Remote Similarity	NPD6273	Approved
0.6416	Remote Similarity	NPD4288	Approved
0.6408	Remote Similarity	NPD9244	Approved
0.6405	Remote Similarity	NPD3092	Approved
0.6398	Remote Similarity	NPD4287	Approved
0.6387	Remote Similarity	NPD1283	Approved
0.638	Remote Similarity	NPD6099	Approved
0.638	Remote Similarity	NPD6100	Approved
0.6369	Remote Similarity	NPD7473	Discontinued
0.6364	Remote Similarity	NPD2800	Approved
0.6358	Remote Similarity	NPD7009	Phase 2
0.6345	Remote Similarity	NPD9266	Approved
0.6345	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD74	Approved
0.6333	Remote Similarity	NPD9493	Approved
0.6331	Remote Similarity	NPD288	Approved
0.633	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1651	Approved
0.6312	Remote Similarity	NPD8032	Phase 2
0.6303	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD4750	Phase 3
0.6296	Remote Similarity	NPD1607	Approved
0.6292	Remote Similarity	NPD6232	Discontinued
0.6289	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD2309	Approved
0.6276	Remote Similarity	NPD9267	Approved
0.6276	Remote Similarity	NPD9263	Approved
0.6276	Remote Similarity	NPD9264	Approved
0.6275	Remote Similarity	NPD3095	Discontinued
0.6275	Remote Similarity	NPD4626	Approved
0.6273	Remote Similarity	NPD4445	Approved
0.6259	Remote Similarity	NPD844	Approved
0.6259	Remote Similarity	NPD1809	Phase 2
0.6258	Remote Similarity	NPD3972	Approved
0.625	Remote Similarity	NPD3764	Approved
0.6242	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD3094	Phase 2
0.6236	Remote Similarity	NPD6959	Discontinued
0.6232	Remote Similarity	NPD845	Approved
0.6228	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD8166	Discontinued
0.6224	Remote Similarity	NPD1929	Approved
0.6224	Remote Similarity	NPD1930	Approved
0.6224	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD7458	Discontinued
0.6221	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD1755	Approved
0.6197	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6651	Approved
0.6194	Remote Similarity	NPD1281	Approved
0.6188	Remote Similarity	NPD7008	Discontinued
0.6176	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD1240	Approved
0.6171	Remote Similarity	NPD7819	Suspended
0.6154	Remote Similarity	NPD4878	Approved
0.6149	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD1471	Phase 3
0.6129	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD3020	Approved
0.6127	Remote Similarity	NPD2066	Phase 3
0.6118	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5710	Approved
0.6111	Remote Similarity	NPD5711	Approved
0.6101	Remote Similarity	NPD4624	Approved
0.6099	Remote Similarity	NPD3495	Discontinued
0.6092	Remote Similarity	NPD7028	Phase 2
0.6087	Remote Similarity	NPD9718	Approved
0.6082	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.608	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD6696	Suspended
0.6062	Remote Similarity	NPD4208	Discontinued
0.6059	Remote Similarity	NPD7236	Approved
0.6049	Remote Similarity	NPD411	Approved
0.6045	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD8313	Approved
0.6043	Remote Similarity	NPD8312	Approved
0.6038	Remote Similarity	NPD2797	Approved
0.6038	Remote Similarity	NPD1203	Approved
0.6033	Remote Similarity	NPD6020	Phase 2
0.6032	Remote Similarity	NPD8150	Discontinued
0.6024	Remote Similarity	NPD1510	Phase 2
0.6022	Remote Similarity	NPD5031	Approved
0.6022	Remote Similarity	NPD5027	Approved
0.6022	Remote Similarity	NPD1161	Approved
0.6022	Remote Similarity	NPD5029	Approved
0.6013	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD7961	Discontinued
0.6	Remote Similarity	NPD4097	Suspended
0.6	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5691	Approved
0.6	Remote Similarity	NPD9261	Approved
0.5989	Remote Similarity	NPD5034	Approved
0.5989	Remote Similarity	NPD4955	Approved
0.5989	Remote Similarity	NPD4954	Approved
0.5989	Remote Similarity	NPD5028	Approved
0.5989	Remote Similarity	NPD5026	Approved
0.5989	Remote Similarity	NPD36	Approved
0.5988	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD9281	Approved
0.5987	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD2629	Approved
0.5977	Remote Similarity	NPD7239	Suspended
0.5976	Remote Similarity	NPD4140	Approved
0.5976	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD2979	Phase 3
0.5976	Remote Similarity	NPD3620	Phase 2
0.5973	Remote Similarity	NPD3021	Approved
0.5973	Remote Similarity	NPD3022	Approved
0.5962	Remote Similarity	NPD1751	Approved
0.5959	Remote Similarity	NPD1237	Approved
0.5957	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD1693	Approved
0.5951	Remote Similarity	NPD3268	Approved
0.5949	Remote Similarity	NPD9717	Approved
0.5948	Remote Similarity	NPD3317	Approved
0.5944	Remote Similarity	NPD1168	Approved
0.5941	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD3750	Approved
0.5941	Remote Similarity	NPD4628	Phase 3
0.5939	Remote Similarity	NPD447	Suspended
0.5936	Remote Similarity	NPD1298	Discontinued
0.5936	Remote Similarity	NPD5030	Phase 2
0.5931	Remote Similarity	NPD1932	Approved
0.5928	Remote Similarity	NPD4308	Phase 3
0.5928	Remote Similarity	NPD7539	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4207	Discontinued
0.5922	Remote Similarity	NPD3882	Suspended
0.592	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD2859	Approved
0.5915	Remote Similarity	NPD2860	Approved
0.5909	Remote Similarity	NPD7340	Approved
0.5909	Remote Similarity	NPD6599	Discontinued
0.5909	Remote Similarity	NPD4380	Phase 2
0.5906	Remote Similarity	NPD2329	Discontinued
0.5901	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD5761	Phase 2
0.5899	Remote Similarity	NPD2801	Approved
0.5899	Remote Similarity	NPD5760	Phase 2
0.5894	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD1551	Phase 2
0.589	Remote Similarity	NPD4625	Phase 3
0.5889	Remote Similarity	NPD3749	Approved
0.5885	Remote Similarity	NPD6836	Approved
0.5885	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD497	Approved
0.5879	Remote Similarity	NPD4060	Phase 1
0.5872	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD1792	Phase 2
0.5866	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD5038	Approved
0.5864	Remote Similarity	NPD5037	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