NPASS Compound

Structure

NPC83242 OpenBabel07101718222D 32 35 0 0 1 0 0 0 0 0999 V2000 -3.4641 0.0000 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 2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 0.8660 -2.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 -1.7321 0.0000 0.0000 C 0 0 2 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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 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 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 28 2 0 0 0 0 16 29 2 0 0 0 0 16 32 1 0 0 0 0 17 22 1 0 0 0 0 17 30 1 6 0 0 0 18 24 1 0 0 0 0 18 25 1 6 0 0 0 19 25 1 6 0 0 0 19 26 1 0 0 0 0 20 26 1 6 0 0 0 20 27 1 0 0 0 0 21 27 1 1 0 0 0 21 32 1 0 0 0 0 22 15 1 1 0 0 0 22 23 1 0 0 0 0 23 27 1 6 0 0 0 23 31 1 0 0 0 0 25 5 1 6 0 0 0 26 6 1 6 0 0 0 27 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.32
Volume:	480.0
LogP:	3.768
LogD:	3.733
LogS:	-4.123
# Rotatable Bonds:	3
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.607
Synthetic Accessibility Score:	4.891
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.736
MDCK Permeability:	1.7500697140349075e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.416
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.223
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.438
Plasma Protein Binding (PPB):	82.4317626953125%
Volume Distribution (VD):	0.734
Pgp-substrate:	23.806438446044922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.268
CYP3A4-inhibitor:	0.256
CYP3A4-substrate:	0.338

ADMET: Excretion

Clearance (CL):	10.318
Half-life (T1/2):	0.395

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.215
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.928
Maximum Recommended Daily Dose:	0.31
Skin Sensitization:	0.568
Carcinogencity:	0.249
Eye Corrosion:	0.968
Eye Irritation:	0.055
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC83242

Natural Product ID:	NPC83242
*Common Name:**	(4As,4Br,6S,6As,7S,8R,9S,10As,10Br,12As)-8-Acetyl-7,9-Dihydroxy-1,1,4A,6A,10B-Pentamethyloctadecahydrochrysen-6-Yl Acetate
IUPAC Name:	[(4aS,4bR,6S,6aS,7S,8R,9S,10aS,10bR,12aS)-8-acetyl-7,9-dihydroxy-1,1,4a,6a,10b-pentamethyl-2,3,4,4b,5,6,7,8,9,10,10a,11,12,12a-tetradecahydrochrysen-6-yl] acetate
Synonyms:
Standard InCHIKey:	GPMXXOUSSHHPDV-ZCEACPIUSA-N
Standard InCHI:	InChI=1S/C27H44O5/c1-15(28)22-17(30)13-20-26(6)12-9-18-24(3,4)10-8-11-25(18,5)19(26)14-21(32-16(2)29)27(20,7)23(22)31/h17-23,30-31H,8-14H2,1-7H3/t17-,18-,19+,20-,21-,22+,23-,25-,26+,27+/m0/s1
SMILES:	CC(=O)[C@@H]1[C@H](C[C@H]2[C@]3(C)CC[C@H]4C(C)(C)CCC[C@]4(C)[C@H]3C[C@@H]([C@]2(C)[C@H]1O)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518242
PubChem CID:	11113118
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO33404	phyllospongia sp.	Species	Thorectidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[12502324]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	30.0	%	PMID[482569]

☑ 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 NPC83242 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	489
0.1-0.2	3266
0.2-0.3	7759
0.3-0.4	14089
0.4-0.5	7444
0.5-0.6	4993
0.6-0.7	3347
0.7-0.8	1234
0.8-0.85	55
0.85-0.9	10
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC219535
0.975	High Similarity	NPC237938
0.9294	High Similarity	NPC88337
0.9294	High Similarity	NPC475211
0.9286	High Similarity	NPC473319
0.9286	High Similarity	NPC131104
0.9286	High Similarity	NPC3032
0.9176	High Similarity	NPC471459
0.9176	High Similarity	NPC67653
0.9036	High Similarity	NPC477434
0.8929	High Similarity	NPC477205
0.881	High Similarity	NPC9060
0.881	High Similarity	NPC473336
0.881	High Similarity	NPC471044
0.881	High Similarity	NPC181871
0.881	High Similarity	NPC473299
0.875	High Similarity	NPC474020
0.8706	High Similarity	NPC473350
0.8706	High Similarity	NPC474572
0.8675	High Similarity	NPC476071
0.8667	High Similarity	NPC287354
0.8667	High Similarity	NPC62407
0.8652	High Similarity	NPC476189
0.8605	High Similarity	NPC302111
0.8571	High Similarity	NPC289486
0.8571	High Similarity	NPC61107
0.8571	High Similarity	NPC163685
0.8556	High Similarity	NPC469982
0.8523	High Similarity	NPC61688
0.8523	High Similarity	NPC477440
0.8523	High Similarity	NPC477443
0.8506	High Similarity	NPC470920
0.8488	Intermediate Similarity	NPC131350
0.8462	Intermediate Similarity	NPC82633
0.8427	Intermediate Similarity	NPC477433
0.8427	Intermediate Similarity	NPC477442
0.8427	Intermediate Similarity	NPC477444
0.8409	Intermediate Similarity	NPC236459
0.8391	Intermediate Similarity	NPC120395
0.8391	Intermediate Similarity	NPC248216
0.8372	Intermediate Similarity	NPC50438
0.837	Intermediate Similarity	NPC235109
0.8315	Intermediate Similarity	NPC24705
0.8315	Intermediate Similarity	NPC56962
0.8313	Intermediate Similarity	NPC31031
0.8313	Intermediate Similarity	NPC243594
0.828	Intermediate Similarity	NPC472145
0.8276	Intermediate Similarity	NPC477445
0.8276	Intermediate Similarity	NPC62572
0.8256	Intermediate Similarity	NPC15091
0.8222	Intermediate Similarity	NPC472146
0.8222	Intermediate Similarity	NPC77756
0.8222	Intermediate Similarity	NPC185529
0.8214	Intermediate Similarity	NPC320144
0.8214	Intermediate Similarity	NPC80891
0.8214	Intermediate Similarity	NPC201276
0.8211	Intermediate Similarity	NPC46848
0.8202	Intermediate Similarity	NPC226491
0.8202	Intermediate Similarity	NPC477614
0.8202	Intermediate Similarity	NPC476435
0.8202	Intermediate Similarity	NPC476379
0.8193	Intermediate Similarity	NPC112463
0.8191	Intermediate Similarity	NPC472144
0.8172	Intermediate Similarity	NPC329910
0.8161	Intermediate Similarity	NPC34984
0.8161	Intermediate Similarity	NPC319909
0.8161	Intermediate Similarity	NPC25037
0.814	Intermediate Similarity	NPC30583
0.8132	Intermediate Similarity	NPC475878
0.8132	Intermediate Similarity	NPC52756
0.8125	Intermediate Similarity	NPC286519
0.8125	Intermediate Similarity	NPC214946
0.8125	Intermediate Similarity	NPC246736
0.8125	Intermediate Similarity	NPC275990
0.8125	Intermediate Similarity	NPC88203
0.8125	Intermediate Similarity	NPC76866
0.8125	Intermediate Similarity	NPC304832
0.8125	Intermediate Similarity	NPC148628
0.8118	Intermediate Similarity	NPC261616
0.8111	Intermediate Similarity	NPC200580
0.8105	Intermediate Similarity	NPC94906
0.8095	Intermediate Similarity	NPC171426
0.8095	Intermediate Similarity	NPC34046
0.8095	Intermediate Similarity	NPC185465
0.8095	Intermediate Similarity	NPC324700
0.8095	Intermediate Similarity	NPC224802
0.8095	Intermediate Similarity	NPC80089
0.8095	Intermediate Similarity	NPC472608
0.8095	Intermediate Similarity	NPC26029
0.809	Intermediate Similarity	NPC263802
0.809	Intermediate Similarity	NPC252714
0.8065	Intermediate Similarity	NPC470232
0.8065	Intermediate Similarity	NPC470229
0.8043	Intermediate Similarity	NPC474379
0.8023	Intermediate Similarity	NPC50658
0.8023	Intermediate Similarity	NPC280781
0.8023	Intermediate Similarity	NPC48756
0.8023	Intermediate Similarity	NPC475743
0.8022	Intermediate Similarity	NPC50443
0.8022	Intermediate Similarity	NPC470114
0.8022	Intermediate Similarity	NPC18536
0.8021	Intermediate Similarity	NPC289148
0.8021	Intermediate Similarity	NPC52899
0.8021	Intermediate Similarity	NPC163963
0.8	Intermediate Similarity	NPC38471
0.8	Intermediate Similarity	NPC162459
0.8	Intermediate Similarity	NPC472028
0.8	Intermediate Similarity	NPC38296
0.8	Intermediate Similarity	NPC471038
0.8	Intermediate Similarity	NPC28864
0.8	Intermediate Similarity	NPC20479
0.8	Intermediate Similarity	NPC98837
0.8	Intermediate Similarity	NPC471221
0.8	Intermediate Similarity	NPC474793
0.7979	Intermediate Similarity	NPC116683
0.7979	Intermediate Similarity	NPC193785
0.7978	Intermediate Similarity	NPC477441
0.7976	Intermediate Similarity	NPC477918
0.7976	Intermediate Similarity	NPC143133
0.7976	Intermediate Similarity	NPC298168
0.7976	Intermediate Similarity	NPC221420
0.7959	Intermediate Similarity	NPC327093
0.7957	Intermediate Similarity	NPC247877
0.7957	Intermediate Similarity	NPC47853
0.7957	Intermediate Similarity	NPC475118
0.7957	Intermediate Similarity	NPC470385
0.7957	Intermediate Similarity	NPC309127
0.7957	Intermediate Similarity	NPC470386
0.7955	Intermediate Similarity	NPC105895
0.7955	Intermediate Similarity	NPC475689
0.7952	Intermediate Similarity	NPC179858
0.7952	Intermediate Similarity	NPC159789
0.7938	Intermediate Similarity	NPC471254
0.7938	Intermediate Similarity	NPC124544
0.7938	Intermediate Similarity	NPC470172
0.7935	Intermediate Similarity	NPC476934
0.7931	Intermediate Similarity	NPC2096
0.7931	Intermediate Similarity	NPC208912
0.7931	Intermediate Similarity	NPC268040
0.7927	Intermediate Similarity	NPC477229
0.7927	Intermediate Similarity	NPC282905
0.7927	Intermediate Similarity	NPC68426
0.7917	Intermediate Similarity	NPC293866
0.7917	Intermediate Similarity	NPC41971
0.7917	Intermediate Similarity	NPC293890
0.7917	Intermediate Similarity	NPC37047
0.7917	Intermediate Similarity	NPC180733
0.7917	Intermediate Similarity	NPC287676
0.7907	Intermediate Similarity	NPC477851
0.7895	Intermediate Similarity	NPC476879
0.7895	Intermediate Similarity	NPC472273
0.7895	Intermediate Similarity	NPC476878
0.7879	Intermediate Similarity	NPC200957
0.7879	Intermediate Similarity	NPC138908
0.7879	Intermediate Similarity	NPC295366
0.7879	Intermediate Similarity	NPC37600
0.7872	Intermediate Similarity	NPC263135
0.7872	Intermediate Similarity	NPC288906
0.7857	Intermediate Similarity	NPC471046
0.7857	Intermediate Similarity	NPC5767
0.7857	Intermediate Similarity	NPC477933
0.7857	Intermediate Similarity	NPC473406
0.7857	Intermediate Similarity	NPC87927
0.7857	Intermediate Similarity	NPC139347
0.7857	Intermediate Similarity	NPC477932
0.7857	Intermediate Similarity	NPC475742
0.7857	Intermediate Similarity	NPC108840
0.7857	Intermediate Similarity	NPC4209
0.7849	Intermediate Similarity	NPC471902
0.7849	Intermediate Similarity	NPC244356
0.7849	Intermediate Similarity	NPC224060
0.7849	Intermediate Similarity	NPC473690
0.7849	Intermediate Similarity	NPC199543
0.7849	Intermediate Similarity	NPC287118
0.7841	Intermediate Similarity	NPC269684
0.7841	Intermediate Similarity	NPC474346
0.7841	Intermediate Similarity	NPC474284
0.7841	Intermediate Similarity	NPC474253
0.7841	Intermediate Similarity	NPC213737
0.7841	Intermediate Similarity	NPC475820
0.7835	Intermediate Similarity	NPC236585
0.7835	Intermediate Similarity	NPC121218
0.7835	Intermediate Similarity	NPC75941
0.7835	Intermediate Similarity	NPC253886
0.7831	Intermediate Similarity	NPC168511
0.7831	Intermediate Similarity	NPC159325
0.7826	Intermediate Similarity	NPC476296
0.7816	Intermediate Similarity	NPC73515
0.7816	Intermediate Similarity	NPC271572
0.7816	Intermediate Similarity	NPC474870
0.7812	Intermediate Similarity	NPC475876
0.7812	Intermediate Similarity	NPC78427
0.7812	Intermediate Similarity	NPC16911
0.7812	Intermediate Similarity	NPC89099
0.78	Intermediate Similarity	NPC166993
0.78	Intermediate Similarity	NPC176949
0.78	Intermediate Similarity	NPC201908
0.7791	Intermediate Similarity	NPC220379
0.7789	Intermediate Similarity	NPC219353
0.7789	Intermediate Similarity	NPC29410

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 NPC83242 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	547
0.1-0.2	3441
0.2-0.3	3258
0.3-0.4	1195
0.4-0.5	368
0.5-0.6	240
0.6-0.7	81
0.7-0.8	20
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
0.8095	Intermediate Similarity	NPD6118	Approved
0.8095	Intermediate Similarity	NPD6697	Approved
0.8095	Intermediate Similarity	NPD6114	Approved
0.8095	Intermediate Similarity	NPD6115	Approved
0.7952	Intermediate Similarity	NPD3703	Phase 2
0.7857	Intermediate Similarity	NPD6117	Approved
0.7765	Intermediate Similarity	NPD6116	Phase 1
0.7619	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7748	Approved
0.7188	Intermediate Similarity	NPD8035	Phase 2
0.7188	Intermediate Similarity	NPD8034	Phase 2
0.7188	Intermediate Similarity	NPD7515	Phase 2
0.7176	Intermediate Similarity	NPD5777	Approved
0.7156	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4245	Approved
0.7059	Intermediate Similarity	NPD4244	Approved
0.7	Intermediate Similarity	NPD7902	Approved
0.6988	Remote Similarity	NPD4224	Phase 2
0.6977	Remote Similarity	NPD6081	Approved
0.6941	Remote Similarity	NPD3698	Phase 2
0.6932	Remote Similarity	NPD3702	Approved
0.693	Remote Similarity	NPD8328	Phase 3
0.686	Remote Similarity	NPD4789	Approved
0.6824	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5360	Phase 3
0.6822	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD1700	Approved
0.6765	Remote Similarity	NPD7638	Approved
0.6754	Remote Similarity	NPD6921	Approved
0.6703	Remote Similarity	NPD3671	Phase 1
0.67	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7900	Approved
0.6699	Remote Similarity	NPD7640	Approved
0.6699	Remote Similarity	NPD7639	Approved
0.6698	Remote Similarity	NPD6675	Approved
0.6698	Remote Similarity	NPD7128	Approved
0.6698	Remote Similarity	NPD6402	Approved
0.6698	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6411	Approved
0.6574	Remote Similarity	NPD7320	Approved
0.6574	Remote Similarity	NPD6899	Approved
0.6574	Remote Similarity	NPD6881	Approved
0.6571	Remote Similarity	NPD7632	Discontinued
0.6559	Remote Similarity	NPD6928	Phase 2
0.6555	Remote Similarity	NPD7736	Approved
0.6552	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8418	Phase 2
0.6522	Remote Similarity	NPD6319	Approved
0.6514	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6372	Approved
0.6514	Remote Similarity	NPD6373	Approved
0.65	Remote Similarity	NPD7319	Approved
0.6481	Remote Similarity	NPD5697	Approved
0.6481	Remote Similarity	NPD5701	Approved
0.6465	Remote Similarity	NPD6101	Approved
0.6465	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5328	Approved
0.6455	Remote Similarity	NPD7290	Approved
0.6455	Remote Similarity	NPD6883	Approved
0.6455	Remote Similarity	NPD7102	Approved
0.6441	Remote Similarity	NPD7492	Approved
0.6436	Remote Similarity	NPD6399	Phase 3
0.6436	Remote Similarity	NPD5778	Approved
0.6436	Remote Similarity	NPD5779	Approved
0.6429	Remote Similarity	NPD8133	Approved
0.6404	Remote Similarity	NPD4758	Discontinued
0.6396	Remote Similarity	NPD6617	Approved
0.6396	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD8130	Phase 1
0.6396	Remote Similarity	NPD6649	Approved
0.6396	Remote Similarity	NPD6847	Approved
0.6396	Remote Similarity	NPD6869	Approved
0.6387	Remote Similarity	NPD6616	Approved
0.6379	Remote Similarity	NPD6059	Approved
0.6379	Remote Similarity	NPD6054	Approved
0.6364	Remote Similarity	NPD6014	Approved
0.6364	Remote Similarity	NPD6012	Approved
0.6364	Remote Similarity	NPD6013	Approved
0.6344	Remote Similarity	NPD4802	Phase 2
0.6344	Remote Similarity	NPD5364	Discontinued
0.6344	Remote Similarity	NPD4238	Approved
0.6339	Remote Similarity	NPD8297	Approved
0.6339	Remote Similarity	NPD6882	Approved
0.6337	Remote Similarity	NPD6079	Approved
0.6333	Remote Similarity	NPD8293	Discontinued
0.6333	Remote Similarity	NPD7078	Approved
0.6316	Remote Similarity	NPD1779	Approved
0.6316	Remote Similarity	NPD1780	Approved
0.6316	Remote Similarity	NPD6940	Discontinued
0.6306	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4632	Approved
0.6277	Remote Similarity	NPD7645	Phase 2
0.6273	Remote Similarity	NPD6011	Approved
0.6271	Remote Similarity	NPD6370	Approved
0.6263	Remote Similarity	NPD3573	Approved
0.6261	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD7507	Approved
0.625	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6008	Approved
0.62	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4755	Approved
0.619	Remote Similarity	NPD6084	Phase 2
0.619	Remote Similarity	NPD6083	Phase 2
0.6186	Remote Similarity	NPD3669	Approved
0.6186	Remote Similarity	NPD6015	Approved
0.6186	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6016	Approved
0.6182	Remote Similarity	NPD6412	Phase 2
0.6163	Remote Similarity	NPD7909	Approved
0.6162	Remote Similarity	NPD3618	Phase 1
0.6161	Remote Similarity	NPD4634	Approved
0.6134	Remote Similarity	NPD5988	Approved
0.6122	Remote Similarity	NPD4786	Approved
0.6121	Remote Similarity	NPD6009	Approved
0.6117	Remote Similarity	NPD8171	Discontinued
0.6111	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5222	Approved
0.6095	Remote Similarity	NPD4697	Phase 3
0.6095	Remote Similarity	NPD5221	Approved
0.6095	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7604	Phase 2
0.6082	Remote Similarity	NPD7345	Approved
0.6082	Remote Similarity	NPD3667	Approved
0.6075	Remote Similarity	NPD5285	Approved
0.6075	Remote Similarity	NPD5286	Approved
0.6075	Remote Similarity	NPD4700	Approved
0.6075	Remote Similarity	NPD4696	Approved
0.6067	Remote Similarity	NPD229	Approved
0.605	Remote Similarity	NPD5983	Phase 2
0.6038	Remote Similarity	NPD5173	Approved
0.6036	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6274	Approved
0.6034	Remote Similarity	NPD6868	Approved
0.602	Remote Similarity	NPD4788	Approved
0.6019	Remote Similarity	NPD7637	Suspended
0.6017	Remote Similarity	NPD7100	Approved
0.6017	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD7521	Approved
0.5984	Remote Similarity	NPD6336	Discontinued
0.5982	Remote Similarity	NPD6686	Approved
0.5981	Remote Similarity	NPD4225	Approved
0.598	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD371	Approved
0.5963	Remote Similarity	NPD5225	Approved
0.5963	Remote Similarity	NPD4633	Approved
0.5963	Remote Similarity	NPD5226	Approved
0.5963	Remote Similarity	NPD5224	Approved
0.5963	Remote Similarity	NPD5211	Phase 2
0.5946	Remote Similarity	NPD6920	Discontinued
0.5934	Remote Similarity	NPD4787	Phase 1
0.5932	Remote Similarity	NPD6335	Approved
0.5917	Remote Similarity	NPD6909	Approved
0.5917	Remote Similarity	NPD6908	Approved
0.5909	Remote Similarity	NPD5174	Approved
0.5909	Remote Similarity	NPD5175	Approved
0.5887	Remote Similarity	NPD6033	Approved
0.5882	Remote Similarity	NPD5737	Approved
0.5882	Remote Similarity	NPD6672	Approved
0.5882	Remote Similarity	NPD3198	Approved
0.5882	Remote Similarity	NPD6903	Approved
0.5872	Remote Similarity	NPD5223	Approved
0.5862	Remote Similarity	NPD8298	Phase 2
0.5856	Remote Similarity	NPD5141	Approved
0.5854	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5695	Phase 3
0.5847	Remote Similarity	NPD6317	Approved
0.5842	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5696	Approved
0.5818	Remote Similarity	NPD8139	Approved
0.5818	Remote Similarity	NPD8086	Approved
0.5818	Remote Similarity	NPD8084	Approved
0.5818	Remote Similarity	NPD8085	Approved
0.5818	Remote Similarity	NPD8082	Approved
0.5818	Remote Similarity	NPD8138	Approved
0.5818	Remote Similarity	NPD8083	Approved
0.581	Remote Similarity	NPD4202	Approved
0.5804	Remote Similarity	NPD4767	Approved
0.5804	Remote Similarity	NPD4768	Approved
0.58	Remote Similarity	NPD3666	Approved
0.58	Remote Similarity	NPD3133	Approved
0.58	Remote Similarity	NPD3665	Phase 1
0.5798	Remote Similarity	NPD7328	Approved
0.5798	Remote Similarity	NPD6314	Approved
0.5798	Remote Similarity	NPD6313	Approved
0.5798	Remote Similarity	NPD7327	Approved
0.5794	Remote Similarity	NPD7614	Phase 1

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