NPASS Compound

Structure

NPC208912 OpenBabel07101719512D 33 37 0 0 1 0 0 0 0 0999 V2000 0.2788 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6728 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 16 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 28 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 25 1 0 0 0 0 11 26 1 0 0 0 0 12 27 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 1 1 1 0 0 0 15 22 1 0 0 0 0 15 32 1 0 0 0 0 16 29 2 0 0 0 0 16 33 1 0 0 0 0 17 22 1 0 0 0 0 17 30 1 1 0 0 0 18 25 1 0 0 0 0 18 26 1 1 0 0 0 19 26 1 1 0 0 0 19 27 1 0 0 0 0 20 27 1 1 0 0 0 20 28 1 0 0 0 0 21 28 1 6 0 0 0 21 33 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 23 28 1 0 0 0 0 24 31 1 0 0 0 0 24 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.33
Volume:	491.376
LogP:	4.906
LogD:	4.007
LogS:	-4.472
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	5.159
Fsp3:	0.964
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:	-4.722
MDCK Permeability:	1.671171594352927e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.295
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.856
30% Bioavailability (F30%):	0.87

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.175
Plasma Protein Binding (PPB):	84.4571304321289%
Volume Distribution (VD):	1.762
Pgp-substrate:	22.58519744873047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.173
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.125
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.289
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	8.942
Half-life (T1/2):	0.146

ADMET: Toxicity

hERG Blockers:	0.467
Human Hepatotoxicity (H-HT):	0.307
Drug-inuced Liver Injury (DILI):	0.258
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.881
Maximum Recommended Daily Dose:	0.094
Skin Sensitization:	0.536
Carcinogencity:	0.241
Eye Corrosion:	0.819
Eye Irritation:	0.047
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC208912

Natural Product ID:	NPC208912
*Common Name:**	(1R,3S,3As,4S,5As,5Br,7As,11As,11Br,13S,13As,13Bs)-1,4-Dihydroxy-3,5B,8,8,11A,13A-Hexamethylicosahydrochryseno[2,1-C]Furan-13-Yl Acetate
IUPAC Name:	[(1R,3S,3aS,4S,5aS,5bR,7aS,11aS,11bR,13S,13aS,13bS)-1,4-dihydroxy-3,5b,8,8,11a,13a-hexamethyl-1,3,3a,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-hexadecahydrophenanthro[2,1-e][2]benzofuran-13-yl] acetate
Synonyms:
Standard InCHIKey:	YXMVZNUXPZBMJR-KCEWOJSZSA-N
Standard InCHI:	InChI=1S/C28H46O5/c1-15-22-17(30)13-20-27(6)12-9-18-25(3,4)10-8-11-26(18,5)19(27)14-21(33-16(2)29)28(20,7)23(22)24(31)32-15/h15,17-24,30-31H,8-14H2,1-7H3/t15-,17-,18-,19+,20-,21-,22+,23+,24+,26-,27+,28+/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@H]2[C@@]([C@H]3[C@@]1(C)[C@H]1[C@H](O)O[C@H]([C@@H]1[C@H](C3)O)C)(C)CC[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464295
PubChem CID:	11005073
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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[564179]

☑ 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 NPC208912 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	404
0.1-0.2	3585
0.2-0.3	11318
0.3-0.4	12535
0.4-0.5	5731
0.5-0.6	3968
0.6-0.7	3618
0.7-0.8	1401
0.8-0.85	107
0.85-0.9	22
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC2096
0.987	High Similarity	NPC474284
0.987	High Similarity	NPC474253
0.987	High Similarity	NPC474346
0.987	High Similarity	NPC475820
0.987	High Similarity	NPC213737
0.9231	High Similarity	NPC475456
0.8795	High Similarity	NPC471410
0.8795	High Similarity	NPC471411
0.878	High Similarity	NPC473299
0.878	High Similarity	NPC18953
0.8675	High Similarity	NPC235402
0.8642	High Similarity	NPC73515
0.8506	High Similarity	NPC475878
0.8471	Intermediate Similarity	NPC213658
0.8471	Intermediate Similarity	NPC45833
0.8471	Intermediate Similarity	NPC110365
0.8471	Intermediate Similarity	NPC62202
0.8395	Intermediate Similarity	NPC220379
0.8391	Intermediate Similarity	NPC50443
0.8391	Intermediate Similarity	NPC18536
0.8372	Intermediate Similarity	NPC470872
0.8352	Intermediate Similarity	NPC471375
0.8352	Intermediate Similarity	NPC471374
0.8352	Intermediate Similarity	NPC209798
0.8333	Intermediate Similarity	NPC203434
0.8333	Intermediate Similarity	NPC237071
0.8333	Intermediate Similarity	NPC238796
0.8315	Intermediate Similarity	NPC151214
0.8315	Intermediate Similarity	NPC191915
0.8293	Intermediate Similarity	NPC471217
0.8293	Intermediate Similarity	NPC471216
0.8293	Intermediate Similarity	NPC472951
0.8293	Intermediate Similarity	NPC472943
0.8272	Intermediate Similarity	NPC477577
0.8261	Intermediate Similarity	NPC51579
0.8261	Intermediate Similarity	NPC471427
0.8261	Intermediate Similarity	NPC471426
0.8261	Intermediate Similarity	NPC471428
0.8235	Intermediate Similarity	NPC290612
0.8222	Intermediate Similarity	NPC94582
0.8222	Intermediate Similarity	NPC21897
0.8222	Intermediate Similarity	NPC57964
0.8193	Intermediate Similarity	NPC271572
0.8193	Intermediate Similarity	NPC71541
0.8193	Intermediate Similarity	NPC474870
0.8171	Intermediate Similarity	NPC476176
0.814	Intermediate Similarity	NPC215968
0.814	Intermediate Similarity	NPC155531
0.8132	Intermediate Similarity	NPC252056
0.8132	Intermediate Similarity	NPC475785
0.8132	Intermediate Similarity	NPC296936
0.8132	Intermediate Similarity	NPC475765
0.8095	Intermediate Similarity	NPC202688
0.8095	Intermediate Similarity	NPC60018
0.8095	Intermediate Similarity	NPC296734
0.8095	Intermediate Similarity	NPC477446
0.8095	Intermediate Similarity	NPC154043
0.8095	Intermediate Similarity	NPC470155
0.8095	Intermediate Similarity	NPC477447
0.8068	Intermediate Similarity	NPC82955
0.8068	Intermediate Similarity	NPC471459
0.8068	Intermediate Similarity	NPC67653
0.8065	Intermediate Similarity	NPC470030
0.8049	Intermediate Similarity	NPC471045
0.8049	Intermediate Similarity	NPC177343
0.8046	Intermediate Similarity	NPC43912
0.8046	Intermediate Similarity	NPC140446
0.8043	Intermediate Similarity	NPC97867
0.8043	Intermediate Similarity	NPC472273
0.8043	Intermediate Similarity	NPC472145
0.8043	Intermediate Similarity	NPC470591
0.8025	Intermediate Similarity	NPC107963
0.8023	Intermediate Similarity	NPC266651
0.8	Intermediate Similarity	NPC475307
0.8	Intermediate Similarity	NPC470623
0.8	Intermediate Similarity	NPC477285
0.8	Intermediate Similarity	NPC323231
0.8	Intermediate Similarity	NPC74639
0.8	Intermediate Similarity	NPC122083
0.8	Intermediate Similarity	NPC182740
0.8	Intermediate Similarity	NPC111582
0.8	Intermediate Similarity	NPC224003
0.8	Intermediate Similarity	NPC211845
0.8	Intermediate Similarity	NPC256104
0.8	Intermediate Similarity	NPC18724
0.8	Intermediate Similarity	NPC171741
0.7979	Intermediate Similarity	NPC475574
0.7979	Intermediate Similarity	NPC476512
0.7979	Intermediate Similarity	NPC472081
0.7979	Intermediate Similarity	NPC108227
0.7978	Intermediate Similarity	NPC473542
0.7976	Intermediate Similarity	NPC470156
0.7976	Intermediate Similarity	NPC470154
0.7957	Intermediate Similarity	NPC292775
0.7957	Intermediate Similarity	NPC472144
0.7955	Intermediate Similarity	NPC263079
0.7955	Intermediate Similarity	NPC281004
0.7935	Intermediate Similarity	NPC156377
0.7931	Intermediate Similarity	NPC83242
0.7931	Intermediate Similarity	NPC477283
0.7927	Intermediate Similarity	NPC212453
0.7922	Intermediate Similarity	NPC476928
0.7912	Intermediate Similarity	NPC267238
0.7912	Intermediate Similarity	NPC253611
0.7912	Intermediate Similarity	NPC77717
0.7912	Intermediate Similarity	NPC471373
0.7912	Intermediate Similarity	NPC148593
0.7907	Intermediate Similarity	NPC237938
0.7907	Intermediate Similarity	NPC219535
0.7907	Intermediate Similarity	NPC299963
0.7895	Intermediate Similarity	NPC134967
0.7895	Intermediate Similarity	NPC114700
0.7895	Intermediate Similarity	NPC470029
0.7895	Intermediate Similarity	NPC310138
0.7889	Intermediate Similarity	NPC149966
0.7889	Intermediate Similarity	NPC59006
0.7889	Intermediate Similarity	NPC5632
0.7889	Intermediate Similarity	NPC229801
0.7889	Intermediate Similarity	NPC210759
0.7889	Intermediate Similarity	NPC307167
0.7882	Intermediate Similarity	NPC286719
0.7882	Intermediate Similarity	NPC477286
0.7882	Intermediate Similarity	NPC470611
0.7875	Intermediate Similarity	NPC253805
0.7872	Intermediate Similarity	NPC161527
0.7872	Intermediate Similarity	NPC219285
0.7872	Intermediate Similarity	NPC228251
0.7872	Intermediate Similarity	NPC477971
0.7872	Intermediate Similarity	NPC477972
0.7872	Intermediate Similarity	NPC146188
0.7872	Intermediate Similarity	NPC317019
0.7872	Intermediate Similarity	NPC477968
0.7872	Intermediate Similarity	NPC20113
0.7865	Intermediate Similarity	NPC131466
0.7865	Intermediate Similarity	NPC102725
0.7865	Intermediate Similarity	NPC473472
0.7865	Intermediate Similarity	NPC20822
0.7857	Intermediate Similarity	NPC186588
0.7857	Intermediate Similarity	NPC474714
0.7857	Intermediate Similarity	NPC7479
0.7857	Intermediate Similarity	NPC248944
0.7857	Intermediate Similarity	NPC257296
0.7849	Intermediate Similarity	NPC278939
0.7849	Intermediate Similarity	NPC471770
0.7849	Intermediate Similarity	NPC210157
0.7849	Intermediate Similarity	NPC473555
0.7841	Intermediate Similarity	NPC252714
0.7826	Intermediate Similarity	NPC106701
0.7826	Intermediate Similarity	NPC189575
0.7826	Intermediate Similarity	NPC205129
0.7826	Intermediate Similarity	NPC471429
0.7826	Intermediate Similarity	NPC471425
0.7826	Intermediate Similarity	NPC471424
0.7816	Intermediate Similarity	NPC232044
0.7816	Intermediate Similarity	NPC273290
0.7812	Intermediate Similarity	NPC97260
0.7812	Intermediate Similarity	NPC476837
0.7812	Intermediate Similarity	NPC139181
0.7805	Intermediate Similarity	NPC136424
0.7802	Intermediate Similarity	NPC311246
0.7802	Intermediate Similarity	NPC149400
0.7802	Intermediate Similarity	NPC88962
0.7802	Intermediate Similarity	NPC144790
0.7802	Intermediate Similarity	NPC167644
0.7791	Intermediate Similarity	NPC241959
0.7789	Intermediate Similarity	NPC476839
0.7789	Intermediate Similarity	NPC476838
0.7778	Intermediate Similarity	NPC223143
0.7778	Intermediate Similarity	NPC308489
0.7778	Intermediate Similarity	NPC65550
0.7778	Intermediate Similarity	NPC470114
0.7778	Intermediate Similarity	NPC471370
0.7778	Intermediate Similarity	NPC279329
0.7778	Intermediate Similarity	NPC471371
0.7766	Intermediate Similarity	NPC157739
0.7765	Intermediate Similarity	NPC476494
0.7765	Intermediate Similarity	NPC48756
0.7765	Intermediate Similarity	NPC475743
0.7765	Intermediate Similarity	NPC280781
0.7765	Intermediate Similarity	NPC190940
0.7755	Intermediate Similarity	NPC126753
0.775	Intermediate Similarity	NPC252182
0.775	Intermediate Similarity	NPC127094
0.775	Intermediate Similarity	NPC470071
0.775	Intermediate Similarity	NPC1340
0.775	Intermediate Similarity	NPC187471
0.7742	Intermediate Similarity	NPC193785
0.7742	Intermediate Similarity	NPC235109
0.7738	Intermediate Similarity	NPC80891
0.7738	Intermediate Similarity	NPC201276
0.7738	Intermediate Similarity	NPC477287
0.7732	Intermediate Similarity	NPC469827
0.7727	Intermediate Similarity	NPC474008
0.7727	Intermediate Similarity	NPC471240
0.7717	Intermediate Similarity	NPC473851
0.7717	Intermediate Similarity	NPC477224
0.7717	Intermediate Similarity	NPC475436
0.7717	Intermediate Similarity	NPC3538
0.7717	Intermediate Similarity	NPC24960

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 NPC208912 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	3753
0.2-0.3	3436
0.3-0.4	890
0.4-0.5	336
0.5-0.6	241
0.6-0.7	69
0.7-0.8	20
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7857	Intermediate Similarity	NPD6928	Phase 2
0.7619	Intermediate Similarity	NPD6697	Approved
0.7619	Intermediate Similarity	NPD6118	Approved
0.7619	Intermediate Similarity	NPD6115	Approved
0.7619	Intermediate Similarity	NPD6114	Approved
0.7609	Intermediate Similarity	NPD8171	Discontinued
0.75	Intermediate Similarity	NPD6116	Phase 1
0.7381	Intermediate Similarity	NPD6117	Approved
0.72	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3669	Approved
0.7	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8034	Phase 2
0.6947	Remote Similarity	NPD8035	Phase 2
0.6941	Remote Similarity	NPD1810	Approved
0.6941	Remote Similarity	NPD1811	Approved
0.6923	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3703	Phase 2
0.6848	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8133	Approved
0.6789	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7991	Discontinued
0.6727	Remote Similarity	NPD7327	Approved
0.6727	Remote Similarity	NPD7328	Approved
0.6706	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7638	Approved
0.6697	Remote Similarity	NPD6940	Discontinued
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD7639	Approved
0.6607	Remote Similarity	NPD8377	Approved
0.6607	Remote Similarity	NPD8294	Approved
0.6588	Remote Similarity	NPD2254	Approved
0.6588	Remote Similarity	NPD2686	Approved
0.6588	Remote Similarity	NPD2687	Approved
0.6556	Remote Similarity	NPD7645	Phase 2
0.6549	Remote Similarity	NPD8296	Approved
0.6549	Remote Similarity	NPD8380	Approved
0.6549	Remote Similarity	NPD8335	Approved
0.6549	Remote Similarity	NPD8379	Approved
0.6549	Remote Similarity	NPD8378	Approved
0.6549	Remote Similarity	NPD8033	Approved
0.6512	Remote Similarity	NPD5777	Approved
0.6505	Remote Similarity	NPD7632	Discontinued
0.6465	Remote Similarity	NPD7748	Approved
0.6436	Remote Similarity	NPD7902	Approved
0.6435	Remote Similarity	NPD8328	Phase 3
0.6429	Remote Similarity	NPD7515	Phase 2
0.6415	Remote Similarity	NPD6412	Phase 2
0.6413	Remote Similarity	NPD1779	Approved
0.6413	Remote Similarity	NPD1780	Approved
0.6395	Remote Similarity	NPD4244	Approved
0.6395	Remote Similarity	NPD4245	Approved
0.6395	Remote Similarity	NPD4787	Phase 1
0.6356	Remote Similarity	NPD7736	Approved
0.6355	Remote Similarity	NPD6686	Approved
0.6325	Remote Similarity	NPD7507	Approved
0.6322	Remote Similarity	NPD6081	Approved
0.631	Remote Similarity	NPD4224	Phase 2
0.6304	Remote Similarity	NPD7525	Registered
0.6292	Remote Similarity	NPD3702	Approved
0.6279	Remote Similarity	NPD3698	Phase 2
0.6265	Remote Similarity	NPD371	Approved
0.6261	Remote Similarity	NPD7503	Approved
0.6207	Remote Similarity	NPD4789	Approved
0.6204	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7319	Approved
0.6163	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD5360	Phase 3
0.6154	Remote Similarity	NPD8418	Phase 2
0.6147	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7900	Approved
0.6139	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8293	Discontinued
0.6087	Remote Similarity	NPD3671	Phase 1
0.6068	Remote Similarity	NPD6370	Approved
0.604	Remote Similarity	NPD6399	Phase 3
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6882	Approved
0.5966	Remote Similarity	NPD7492	Approved
0.5946	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD1700	Approved
0.5917	Remote Similarity	NPD6616	Approved
0.5909	Remote Similarity	NPD6881	Approved
0.5909	Remote Similarity	NPD6899	Approved
0.5909	Remote Similarity	NPD7320	Approved
0.5905	Remote Similarity	NPD4225	Approved
0.5897	Remote Similarity	NPD6059	Approved
0.5897	Remote Similarity	NPD6054	Approved
0.5882	Remote Similarity	NPD6067	Discontinued
0.5868	Remote Similarity	NPD7078	Approved
0.5856	Remote Similarity	NPD6372	Approved
0.5856	Remote Similarity	NPD6373	Approved
0.5842	Remote Similarity	NPD6700	Approved
0.5842	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5697	Approved
0.5818	Remote Similarity	NPD5701	Approved
0.5818	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD7102	Approved
0.5804	Remote Similarity	NPD7290	Approved
0.5804	Remote Similarity	NPD6883	Approved
0.5784	Remote Similarity	NPD6703	Approved
0.5784	Remote Similarity	NPD6702	Approved
0.5778	Remote Similarity	NPD4758	Discontinued
0.5776	Remote Similarity	NPD6009	Approved
0.5766	Remote Similarity	NPD8174	Phase 2
0.5758	Remote Similarity	NPD8308	Discontinued
0.5752	Remote Similarity	NPD8130	Phase 1
0.5752	Remote Similarity	NPD6650	Approved
0.5752	Remote Similarity	NPD6617	Approved
0.5752	Remote Similarity	NPD6869	Approved
0.5752	Remote Similarity	NPD6649	Approved
0.5752	Remote Similarity	NPD6847	Approved
0.5745	Remote Similarity	NPD4238	Approved
0.5745	Remote Similarity	NPD4802	Phase 2
0.5745	Remote Similarity	NPD5364	Discontinued
0.5727	Remote Similarity	NPD6008	Approved
0.5714	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6015	Approved
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD6016	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.5702	Remote Similarity	NPD8297	Approved
0.5684	Remote Similarity	NPD5354	Approved
0.5676	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5988	Approved
0.566	Remote Similarity	NPD6084	Phase 2
0.566	Remote Similarity	NPD6083	Phase 2
0.5658	Remote Similarity	NPD385	Approved
0.5658	Remote Similarity	NPD384	Approved
0.5652	Remote Similarity	NPD4632	Approved
0.5644	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD7637	Suspended
0.563	Remote Similarity	NPD6319	Approved
0.5625	Remote Similarity	NPD6011	Approved
0.5618	Remote Similarity	NPD229	Approved
0.5614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD6695	Phase 3
0.561	Remote Similarity	NPD2267	Suspended
0.56	Remote Similarity	NPD3618	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