NPASS Compound

Structure

NPC291875 OpenBabel07101718222D 33 35 0 0 1 0 0 0 0 0999 V2000 4.9049 3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.5000 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 -1.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9049 3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 2.7321 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 -0.5878 -0.8090 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 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 -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 2.4049 2.7321 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 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 -0.0000 -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 0.5000 -3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 0.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 3.5981 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 0.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 4 15 2 0 0 0 0 5 16 1 0 0 0 0 6 25 1 0 0 0 0 7 26 1 0 0 0 0 8 9 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 13 26 1 0 0 0 0 15 17 1 0 0 0 0 16 27 2 0 0 0 0 16 32 1 0 0 0 0 17 28 1 6 0 0 0 18 21 1 0 0 0 0 18 29 1 1 0 0 0 19 12 1 6 0 0 0 19 23 1 0 0 0 0 19 31 1 0 0 0 0 20 30 2 0 0 0 0 20 33 1 0 0 0 0 21 14 1 6 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 26 1 0 0 0 0 24 25 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.29
Volume:	486.205
LogP:	3.188
LogD:	2.579
LogS:	-3.54
# Rotatable Bonds:	7
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.472
Synthetic Accessibility Score:	6.237
Fsp3:	0.846
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:	-4.767
MDCK Permeability:	4.894676385447383e-05
Pgp-inhibitor:	0.204
Pgp-substrate:	0.846
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	64.33973693847656%
Volume Distribution (VD):	1.141
Pgp-substrate:	23.219240188598633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.529
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.343
CYP3A4-substrate:	0.433

ADMET: Excretion

Clearance (CL):	6.093
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.227
Human Hepatotoxicity (H-HT):	0.871
Drug-inuced Liver Injury (DILI):	0.879
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.388
Maximum Recommended Daily Dose:	0.405
Skin Sensitization:	0.136
Carcinogencity:	0.118
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.654

Download Data

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

Natural Product: NPC291875

Natural Product ID:	NPC291875
*Common Name:**	Pachycladin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YXHDJJFBUUGCHE-XWJYJYPBSA-N
Standard InCHI:	InChI=1S/C26H42O7/c1-8-9-20(30)33-26(7)13-18(29)21(14(2)3)22-23(26)19-12-15(4)17(28)10-11-25(6,24(22)31-19)32-16(5)27/h14,17-19,21-24,28-29H,4,8-13H2,1-3,5-7H3/t17-,18+,19+,21-,22+,23+,24+,25+,26+/m0/s1
SMILES:	CCCC(=O)O[C@]1(C)C[C@H]([C@H](C(C)C)[C@@H]2[C@H]1[C@H]1CC(=C)[C@H](CC[C@](C)([C@@H]2O1)OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096780
PubChem CID:	46833115
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002916] Eunicellane and asbestinane diterpenoids

*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
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	Eukaryota	n.a.	red sea soft coral	n.a.	PMID[20420415]
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	88000.0	nM	PMID[472785]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	11363627.79	nM	PMID[472785]

☑ 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 NPC291875 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	187
0.1-0.2	1501
0.2-0.3	5180
0.3-0.4	12834
0.4-0.5	10081
0.5-0.6	7376
0.6-0.7	5068
0.7-0.8	416
0.8-0.85	24
0.85-0.9	11
0.9-0.95	15
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.988	High Similarity	NPC92370
0.9759	High Similarity	NPC44538
0.9639	High Similarity	NPC475684
0.9419	High Similarity	NPC471378
0.9419	High Similarity	NPC312471
0.9412	High Similarity	NPC476724
0.9412	High Similarity	NPC470260
0.9412	High Similarity	NPC75443
0.9412	High Similarity	NPC476723
0.931	High Similarity	NPC91251
0.9302	High Similarity	NPC161560
0.9286	High Similarity	NPC471379
0.9286	High Similarity	NPC196911
0.9277	High Similarity	NPC5958
0.9091	High Similarity	NPC122057
0.9091	High Similarity	NPC312805
0.9048	High Similarity	NPC239308
0.9036	High Similarity	NPC77003
0.8953	High Similarity	NPC322922
0.8953	High Similarity	NPC321812
0.8837	High Similarity	NPC476725
0.8824	High Similarity	NPC127917
0.881	High Similarity	NPC118116
0.8804	High Similarity	NPC111348
0.8617	High Similarity	NPC272223
0.8557	High Similarity	NPC470263
0.8539	High Similarity	NPC309656
0.8488	Intermediate Similarity	NPC103171
0.8462	Intermediate Similarity	NPC8729
0.8462	Intermediate Similarity	NPC208839
0.8452	Intermediate Similarity	NPC252483
0.8452	Intermediate Similarity	NPC191345
0.8387	Intermediate Similarity	NPC476720
0.8372	Intermediate Similarity	NPC211049
0.8352	Intermediate Similarity	NPC153853
0.8261	Intermediate Similarity	NPC165180
0.8242	Intermediate Similarity	NPC194642
0.8235	Intermediate Similarity	NPC43463
0.8235	Intermediate Similarity	NPC264610
0.8214	Intermediate Similarity	NPC136424
0.8214	Intermediate Similarity	NPC329626
0.8214	Intermediate Similarity	NPC293223
0.8211	Intermediate Similarity	NPC473244
0.8161	Intermediate Similarity	NPC116320
0.8161	Intermediate Similarity	NPC119922
0.8111	Intermediate Similarity	NPC214315
0.8105	Intermediate Similarity	NPC284518
0.8095	Intermediate Similarity	NPC36479
0.8085	Intermediate Similarity	NPC476722
0.8065	Intermediate Similarity	NPC41838
0.8021	Intermediate Similarity	NPC473963
0.8	Intermediate Similarity	NPC157686
0.8	Intermediate Similarity	NPC241047
0.8	Intermediate Similarity	NPC259042
0.798	Intermediate Similarity	NPC61442
0.7979	Intermediate Similarity	NPC147272
0.7979	Intermediate Similarity	NPC26046
0.7959	Intermediate Similarity	NPC308824
0.7957	Intermediate Similarity	NPC219937
0.7957	Intermediate Similarity	NPC123252
0.7957	Intermediate Similarity	NPC194485
0.7957	Intermediate Similarity	NPC48732
0.7957	Intermediate Similarity	NPC53890
0.7917	Intermediate Similarity	NPC284194
0.7917	Intermediate Similarity	NPC169270
0.7917	Intermediate Similarity	NPC471765
0.7917	Intermediate Similarity	NPC306797
0.7917	Intermediate Similarity	NPC292718
0.7917	Intermediate Similarity	NPC111834
0.7917	Intermediate Similarity	NPC211810
0.7917	Intermediate Similarity	NPC221801
0.7917	Intermediate Similarity	NPC93245
0.7917	Intermediate Similarity	NPC473964
0.7907	Intermediate Similarity	NPC476719
0.7895	Intermediate Similarity	NPC225474
0.7895	Intermediate Similarity	NPC476716
0.7895	Intermediate Similarity	NPC24861
0.7895	Intermediate Similarity	NPC148000
0.7895	Intermediate Similarity	NPC469596
0.7872	Intermediate Similarity	NPC219516
0.7857	Intermediate Similarity	NPC38855
0.7841	Intermediate Similarity	NPC186594
0.7835	Intermediate Similarity	NPC474395
0.7835	Intermediate Similarity	NPC472998
0.7812	Intermediate Similarity	NPC86893
0.7812	Intermediate Similarity	NPC292178
0.7802	Intermediate Similarity	NPC476715
0.7802	Intermediate Similarity	NPC164424
0.78	Intermediate Similarity	NPC475334
0.78	Intermediate Similarity	NPC156681
0.78	Intermediate Similarity	NPC473694
0.78	Intermediate Similarity	NPC475623
0.78	Intermediate Similarity	NPC72842
0.78	Intermediate Similarity	NPC99510
0.7789	Intermediate Similarity	NPC99653
0.7788	Intermediate Similarity	NPC157476
0.7778	Intermediate Similarity	NPC98225
0.7767	Intermediate Similarity	NPC154906
0.7766	Intermediate Similarity	NPC10274
0.7745	Intermediate Similarity	NPC67321
0.7745	Intermediate Similarity	NPC187435
0.7742	Intermediate Similarity	NPC160304
0.7732	Intermediate Similarity	NPC256227
0.7732	Intermediate Similarity	NPC472995
0.7723	Intermediate Similarity	NPC201144
0.7723	Intermediate Similarity	NPC475331
0.7723	Intermediate Similarity	NPC80809
0.7723	Intermediate Similarity	NPC121518
0.7723	Intermediate Similarity	NPC181104
0.7723	Intermediate Similarity	NPC103298
0.7723	Intermediate Similarity	NPC288502
0.7723	Intermediate Similarity	NPC475335
0.7717	Intermediate Similarity	NPC235196
0.7717	Intermediate Similarity	NPC228593
0.7708	Intermediate Similarity	NPC3359
0.7708	Intermediate Similarity	NPC472416
0.7708	Intermediate Similarity	NPC472360
0.77	Intermediate Similarity	NPC472552
0.77	Intermediate Similarity	NPC164551
0.7692	Intermediate Similarity	NPC97505
0.7692	Intermediate Similarity	NPC299963
0.7684	Intermediate Similarity	NPC130840
0.7684	Intermediate Similarity	NPC473675
0.7684	Intermediate Similarity	NPC471747
0.7684	Intermediate Similarity	NPC124374
0.7677	Intermediate Similarity	NPC188968
0.7677	Intermediate Similarity	NPC477655
0.7677	Intermediate Similarity	NPC47024
0.7677	Intermediate Similarity	NPC477656
0.767	Intermediate Similarity	NPC472218
0.767	Intermediate Similarity	NPC472219
0.767	Intermediate Similarity	NPC37628
0.767	Intermediate Similarity	NPC472217
0.767	Intermediate Similarity	NPC38948
0.7667	Intermediate Similarity	NPC216800
0.766	Intermediate Similarity	NPC246028
0.766	Intermediate Similarity	NPC77001
0.766	Intermediate Similarity	NPC253618
0.7653	Intermediate Similarity	NPC120446
0.7653	Intermediate Similarity	NPC136781
0.7653	Intermediate Similarity	NPC253586
0.7653	Intermediate Similarity	NPC274793
0.7653	Intermediate Similarity	NPC254121
0.7647	Intermediate Similarity	NPC111952
0.7647	Intermediate Similarity	NPC476718
0.7647	Intermediate Similarity	NPC60315
0.7629	Intermediate Similarity	NPC469583
0.7629	Intermediate Similarity	NPC276110
0.76	Intermediate Similarity	NPC121218
0.76	Intermediate Similarity	NPC49532
0.76	Intermediate Similarity	NPC144486
0.76	Intermediate Similarity	NPC475958
0.76	Intermediate Similarity	NPC242666
0.76	Intermediate Similarity	NPC472554
0.76	Intermediate Similarity	NPC253886
0.7596	Intermediate Similarity	NPC206618
0.7596	Intermediate Similarity	NPC42662
0.7579	Intermediate Similarity	NPC475776
0.7579	Intermediate Similarity	NPC220216
0.7579	Intermediate Similarity	NPC471370
0.7579	Intermediate Similarity	NPC209816
0.7579	Intermediate Similarity	NPC471371
0.7576	Intermediate Similarity	NPC216478
0.7576	Intermediate Similarity	NPC476807
0.7576	Intermediate Similarity	NPC476806
0.7576	Intermediate Similarity	NPC469725
0.7573	Intermediate Similarity	NPC284732
0.7573	Intermediate Similarity	NPC143609
0.7573	Intermediate Similarity	NPC78966
0.7551	Intermediate Similarity	NPC472997
0.7551	Intermediate Similarity	NPC475304
0.7551	Intermediate Similarity	NPC472996
0.7551	Intermediate Similarity	NPC165528
0.7551	Intermediate Similarity	NPC228766
0.7551	Intermediate Similarity	NPC129569
0.7549	Intermediate Similarity	NPC474550
0.7549	Intermediate Similarity	NPC473577
0.7549	Intermediate Similarity	NPC283850
0.7549	Intermediate Similarity	NPC475585
0.7549	Intermediate Similarity	NPC473543
0.7526	Intermediate Similarity	NPC182826
0.7526	Intermediate Similarity	NPC105375
0.7526	Intermediate Similarity	NPC39453
0.7526	Intermediate Similarity	NPC96736
0.7526	Intermediate Similarity	NPC178949
0.7525	Intermediate Similarity	NPC31085
0.7525	Intermediate Similarity	NPC238397
0.7525	Intermediate Similarity	NPC471363
0.7525	Intermediate Similarity	NPC476081
0.75	Intermediate Similarity	NPC128795
0.75	Intermediate Similarity	NPC222634
0.75	Intermediate Similarity	NPC217921
0.75	Intermediate Similarity	NPC198054
0.75	Intermediate Similarity	NPC306265
0.75	Intermediate Similarity	NPC249034
0.75	Intermediate Similarity	NPC475963
0.75	Intermediate Similarity	NPC475877
0.75	Intermediate Similarity	NPC102048
0.75	Intermediate Similarity	NPC135015
0.75	Intermediate Similarity	NPC151176

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 NPC291875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	2140
0.2-0.3	3862
0.3-0.4	2035
0.4-0.5	535
0.5-0.6	288
0.6-0.7	109
0.7-0.8	1
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
0.7426	Intermediate Similarity	NPD5344	Discontinued
0.7228	Intermediate Similarity	NPD4225	Approved
0.7157	Intermediate Similarity	NPD6648	Approved
0.7157	Intermediate Similarity	NPD7640	Approved
0.7157	Intermediate Similarity	NPD7639	Approved
0.7059	Intermediate Similarity	NPD7638	Approved
0.7009	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8133	Approved
0.68	Remote Similarity	NPD8034	Phase 2
0.68	Remote Similarity	NPD7637	Suspended
0.68	Remote Similarity	NPD8035	Phase 2
0.6771	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7524	Approved
0.6735	Remote Similarity	NPD4250	Approved
0.6735	Remote Similarity	NPD4251	Approved
0.6733	Remote Similarity	NPD5778	Approved
0.6733	Remote Similarity	NPD5779	Approved
0.6727	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6698	Approved
0.67	Remote Similarity	NPD46	Approved
0.6698	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD6695	Phase 3
0.6634	Remote Similarity	NPD7983	Approved
0.6633	Remote Similarity	NPD4249	Approved
0.6609	Remote Similarity	NPD7328	Approved
0.6609	Remote Similarity	NPD7327	Approved
0.6569	Remote Similarity	NPD6399	Phase 3
0.6552	Remote Similarity	NPD7516	Approved
0.6545	Remote Similarity	NPD6686	Approved
0.6535	Remote Similarity	NPD3168	Discontinued
0.6535	Remote Similarity	NPD7838	Discovery
0.6526	Remote Similarity	NPD4822	Approved
0.6526	Remote Similarity	NPD4819	Approved
0.6526	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4821	Approved
0.6526	Remote Similarity	NPD4820	Approved
0.6522	Remote Similarity	NPD7115	Discovery
0.6514	Remote Similarity	NPD6675	Approved
0.6514	Remote Similarity	NPD7128	Approved
0.6514	Remote Similarity	NPD6402	Approved
0.6514	Remote Similarity	NPD5739	Approved
0.6486	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.646	Remote Similarity	NPD8297	Approved
0.6455	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD8378	Approved
0.6441	Remote Similarity	NPD8515	Approved
0.6441	Remote Similarity	NPD8380	Approved
0.6441	Remote Similarity	NPD8379	Approved
0.6441	Remote Similarity	NPD8517	Approved
0.6441	Remote Similarity	NPD8335	Approved
0.6441	Remote Similarity	NPD8516	Approved
0.6441	Remote Similarity	NPD8296	Approved
0.6441	Remote Similarity	NPD8513	Phase 3
0.6441	Remote Similarity	NPD8033	Approved
0.6417	Remote Similarity	NPD7492	Approved
0.6415	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4632	Approved
0.64	Remote Similarity	NPD7750	Discontinued
0.6396	Remote Similarity	NPD6899	Approved
0.6396	Remote Similarity	NPD6881	Approved
0.6396	Remote Similarity	NPD7320	Approved
0.6372	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6008	Approved
0.6364	Remote Similarity	NPD6616	Approved
0.6364	Remote Similarity	NPD7507	Approved
0.6356	Remote Similarity	NPD8377	Approved
0.6356	Remote Similarity	NPD6059	Approved
0.6356	Remote Similarity	NPD6319	Approved
0.6356	Remote Similarity	NPD6054	Approved
0.6356	Remote Similarity	NPD8294	Approved
0.6354	Remote Similarity	NPD6931	Approved
0.6354	Remote Similarity	NPD6930	Phase 2
0.6354	Remote Similarity	NPD7525	Registered
0.6346	Remote Similarity	NPD7748	Approved
0.6341	Remote Similarity	NPD7319	Approved
0.6339	Remote Similarity	NPD6373	Approved
0.6339	Remote Similarity	NPD6372	Approved
0.6327	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7154	Phase 3
0.6327	Remote Similarity	NPD3669	Approved
0.6322	Remote Similarity	NPD371	Approved
0.6321	Remote Similarity	NPD7902	Approved
0.6316	Remote Similarity	NPD6115	Approved
0.6316	Remote Similarity	NPD6053	Discontinued
0.6316	Remote Similarity	NPD6118	Approved
0.6316	Remote Similarity	NPD4268	Approved
0.6316	Remote Similarity	NPD4271	Approved
0.6316	Remote Similarity	NPD6114	Approved
0.6316	Remote Similarity	NPD6697	Approved
0.6311	Remote Similarity	NPD7515	Phase 2
0.6311	Remote Similarity	NPD7078	Approved
0.6311	Remote Similarity	NPD8293	Discontinued
0.6306	Remote Similarity	NPD5701	Approved
0.6306	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6412	Phase 2
0.6306	Remote Similarity	NPD5697	Approved
0.6303	Remote Similarity	NPD6921	Approved
0.6283	Remote Similarity	NPD7102	Approved
0.6283	Remote Similarity	NPD6371	Approved
0.6283	Remote Similarity	NPD6883	Approved
0.6283	Remote Similarity	NPD7290	Approved
0.6275	Remote Similarity	NPD6101	Approved
0.6275	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7736	Approved
0.625	Remote Similarity	NPD6929	Approved
0.625	Remote Similarity	NPD6370	Approved
0.6239	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6617	Approved
0.6228	Remote Similarity	NPD6650	Approved
0.6228	Remote Similarity	NPD8130	Phase 1
0.6228	Remote Similarity	NPD6649	Approved
0.6228	Remote Similarity	NPD6869	Approved
0.6228	Remote Similarity	NPD6847	Approved
0.6211	Remote Similarity	NPD6116	Phase 1
0.6198	Remote Similarity	NPD7604	Phase 2
0.6195	Remote Similarity	NPD6014	Approved
0.6195	Remote Similarity	NPD6013	Approved
0.6195	Remote Similarity	NPD6012	Approved
0.6179	Remote Similarity	NPD8074	Phase 3
0.6174	Remote Similarity	NPD6882	Approved
0.6168	Remote Similarity	NPD6084	Phase 2
0.6168	Remote Similarity	NPD6083	Phase 2
0.6167	Remote Similarity	NPD6015	Approved
0.6167	Remote Similarity	NPD6016	Approved
0.6167	Remote Similarity	NPD5983	Phase 2
0.6167	Remote Similarity	NPD7503	Approved
0.6163	Remote Similarity	NPD1145	Discontinued
0.6162	Remote Similarity	NPD5362	Discontinued
0.6154	Remote Similarity	NPD7087	Discontinued
0.6154	Remote Similarity	NPD6411	Approved
0.6147	Remote Similarity	NPD1700	Approved
0.6116	Remote Similarity	NPD5988	Approved
0.6106	Remote Similarity	NPD6011	Approved
0.6105	Remote Similarity	NPD6117	Approved
0.61	Remote Similarity	NPD4786	Approved
0.6098	Remote Similarity	NPD6336	Discontinued
0.6091	Remote Similarity	NPD5211	Phase 2
0.6087	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD7645	Phase 2
0.6071	Remote Similarity	NPD5357	Phase 1
0.6066	Remote Similarity	NPD8328	Phase 3
0.6061	Remote Similarity	NPD6435	Approved
0.6061	Remote Similarity	NPD3667	Approved
0.6042	Remote Similarity	NPD5776	Phase 2
0.6042	Remote Similarity	NPD6925	Approved
0.604	Remote Similarity	NPD6893	Approved
0.604	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.604	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7900	Approved
0.6038	Remote Similarity	NPD5282	Discontinued
0.6038	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7514	Phase 3
0.602	Remote Similarity	NPD7332	Phase 2
0.6019	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD5331	Approved
0.6	Remote Similarity	NPD5332	Approved
0.5982	Remote Similarity	NPD5141	Approved
0.5981	Remote Similarity	NPD5695	Phase 3
0.598	Remote Similarity	NPD3618	Phase 1
0.5979	Remote Similarity	NPD7145	Approved
0.5962	Remote Similarity	NPD1695	Approved
0.5962	Remote Similarity	NPD5328	Approved
0.596	Remote Similarity	NPD6898	Phase 1
0.596	Remote Similarity	NPD5369	Approved
0.596	Remote Similarity	NPD4790	Discontinued
0.5943	Remote Similarity	NPD4202	Approved
0.5935	Remote Similarity	NPD6067	Discontinued
0.5926	Remote Similarity	NPD7839	Suspended
0.5922	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5285	Approved
0.5909	Remote Similarity	NPD5286	Approved
0.5909	Remote Similarity	NPD4696	Approved
0.5909	Remote Similarity	NPD4700	Approved
0.59	Remote Similarity	NPD4270	Approved
0.59	Remote Similarity	NPD4269	Approved
0.5895	Remote Similarity	NPD1810	Approved
0.5895	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD1811	Approved
0.5882	Remote Similarity	NPD6274	Approved
0.5876	Remote Similarity	NPD6932	Approved
0.5873	Remote Similarity	NPD6033	Approved
0.5868	Remote Similarity	NPD7101	Approved
0.5868	Remote Similarity	NPD7100	Approved
0.5862	Remote Similarity	NPD4634	Approved
0.5859	Remote Similarity	NPD5368	Approved
0.5849	Remote Similarity	NPD6079	Approved
0.5842	Remote Similarity	NPD4788	Approved
0.5833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7339	Approved
0.5833	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6942	Approved
0.5825	Remote Similarity	NPD7521	Approved
0.5825	Remote Similarity	NPD6409	Approved
0.5825	Remote Similarity	NPD6684	Approved
0.5825	Remote Similarity	NPD7146	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