NPASS Compound

Structure

NPC473585 OpenBabel07101718312D 39 43 0 0 1 0 0 0 0 0999 V2000 4.1160 -5.9679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2500 -2.7359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6160 -5.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7141 -3.7359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8480 -6.2359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8121 -1.6970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7141 -5.7359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5031 -2.6481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9820 -5.7359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6160 -5.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9820 -2.7359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1160 -4.2359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1160 -4.2359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8480 -3.2359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8121 -1.6970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1160 -4.2359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5801 -4.2359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4385 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6215 -3.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6160 -5.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1160 -3.2359 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.7141 -4.7359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3121 -3.2359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9820 -4.7359 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0227 -2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9738 -2.1473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2796 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3121 -4.2359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1160 -4.2359 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.8480 -4.2359 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.7169 -2.8164 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 13.1211 -2.6481 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1817 -1.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4875 -0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4135 -2.2872 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 2.6160 -3.3698 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 13.1782 -4.7359 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 11.4461 -4.7359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 36 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 23 2 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 21 2 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 33 2 0 0 0 0 17 37 1 0 0 0 0 18 23 1 0 0 0 0 18 39 1 0 0 0 0 19 34 2 0 0 0 0 19 35 1 0 0 0 0 20 36 2 0 0 0 0 20 37 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 29 2 0 0 0 0 24 33 1 0 0 0 0 25 30 1 0 0 0 0 25 31 1 0 0 0 0 26 27 2 0 0 0 0 26 28 1 0 0 0 0 26 37 1 0 0 0 0 27 32 1 0 0 0 0 27 34 1 0 0 0 0 28 35 2 0 0 0 0 28 36 1 0 0 0 0 29 38 1 0 0 0 0 29 39 1 0 0 0 0 M CHG 2 36 1 38 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.34
Volume:	561.783
LogP:	3.088
LogD:	3.772
LogS:	-2.796
# Rotatable Bonds:	8
TPSA:	105.99
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.301
Synthetic Accessibility Score:	5.595
Fsp3:	0.548
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.352
MDCK Permeability:	9.475477781961672e-06
Pgp-inhibitor:	0.057
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.942
20% Bioavailability (F20%):	0.501
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.466
Plasma Protein Binding (PPB):	75.87708282470703%
Volume Distribution (VD):	1.1
Pgp-substrate:	26.440937042236328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.867
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.238

ADMET: Excretion

Clearance (CL):	4.77
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.978
Drug-inuced Liver Injury (DILI):	0.852
AMES Toxicity:	0.952
Rat Oral Acute Toxicity:	0.953
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.91
Carcinogencity:	0.541
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.747

Download Data

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

Natural Product: NPC473585

Natural Product ID:	NPC473585
*Common Name:**	Ageline B
IUPAC Name:	[(4aS,5R,6S,8aR)-5-[(E)-5-(6-amino-9-methylpurin-9-ium-7-yl)-3-methylpent-3-enyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl 1H-pyrrole-2-carboxylate;chloride
Synonyms:
Standard InCHIKey:	RACHZHDKVSXFEB-FOJJAWQWSA-N
Standard InCHI:	InChI=1S/C31H42N6O2.ClH/c1-21(13-17-37-20-36(5)28-26(37)27(32)34-19-35-28)11-14-30(3)22(2)12-15-31(4)23(8-6-10-25(30)31)18-39-29(38)24-9-7-16-33-24;/h7-9,13,16,19-20,22,25H,6,10-12,14-15,17-18H2,1-5H3,(H2-,32,33,34,35,38);1H/b21-13+;/t22-,25-,30+,31-;/m0./s1
SMILES:	C/C(=CCn1c[n+](C)c2c1c(N)ncn2)/CC[C@]1(C)[C@@H](C)CC[C@@]2(C)C(=CCC[C@@H]12)COC(=C1C=CC=N1)[O-].Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446524
PubChem CID:	10325639
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	at a depth of 14 m near the island of Ambon (Seram Seilale), Indonesia	1997-AUG	PMID[10514317]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14677933]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332839]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562840]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19209898]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[26083682]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584409]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	papua new guinean	n.a.	PMID[9784179]
NPO11199	Agelas nakamurai	Species	Agelasidae	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
Individual Protein	1
NON-MOLECULAR	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	24000.0	nM	PMID[558148]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IZ	=	12.0	mm	PMID[558148]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IZ	=	9.0	mm	PMID[558148]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[558148]

☑ 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 NPC473585 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	425
0.1-0.2	1928
0.2-0.3	22387
0.3-0.4	14030
0.4-0.5	3320
0.5-0.6	562
0.6-0.7	24
0.7-0.8	18
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9518	High Similarity	NPC265111
0.825	Intermediate Similarity	NPC476521
0.8242	Intermediate Similarity	NPC472834
0.8187	Intermediate Similarity	NPC476013
0.8187	Intermediate Similarity	NPC476522
0.8187	Intermediate Similarity	NPC474986
0.8075	Intermediate Similarity	NPC476520
0.8012	Intermediate Similarity	NPC476433
0.8012	Intermediate Similarity	NPC476528
0.8	Intermediate Similarity	NPC470266
0.7937	Intermediate Similarity	NPC296437
0.7927	Intermediate Similarity	NPC476408
0.7836	Intermediate Similarity	NPC472832
0.7836	Intermediate Similarity	NPC18308
0.7661	Intermediate Similarity	NPC472833
0.7456	Intermediate Similarity	NPC244700
0.7018	Intermediate Similarity	NPC217656
0.6879	Remote Similarity	NPC89139
0.6788	Remote Similarity	NPC101676
0.6718	Remote Similarity	NPC133782
0.6718	Remote Similarity	NPC144474
0.6718	Remote Similarity	NPC527
0.665	Remote Similarity	NPC233431
0.665	Remote Similarity	NPC300139
0.6649	Remote Similarity	NPC477119
0.6633	Remote Similarity	NPC313514
0.6447	Remote Similarity	NPC477118
0.6414	Remote Similarity	NPC477120
0.6396	Remote Similarity	NPC160666
0.6373	Remote Similarity	NPC317054
0.634	Remote Similarity	NPC164845
0.6337	Remote Similarity	NPC57279
0.6329	Remote Similarity	NPC276373
0.6298	Remote Similarity	NPC5802
0.6268	Remote Similarity	NPC157821
0.623	Remote Similarity	NPC150853
0.6205	Remote Similarity	NPC313897
0.6203	Remote Similarity	NPC239737
0.618	Remote Similarity	NPC167285
0.6164	Remote Similarity	NPC250178
0.6133	Remote Similarity	NPC115595
0.6124	Remote Similarity	NPC129756
0.6089	Remote Similarity	NPC317821
0.6089	Remote Similarity	NPC226184
0.6089	Remote Similarity	NPC76544
0.6067	Remote Similarity	NPC33996
0.6032	Remote Similarity	NPC93365
0.6	Remote Similarity	NPC161659
0.6	Remote Similarity	NPC209525
0.599	Remote Similarity	NPC24589
0.5934	Remote Similarity	NPC314152
0.5934	Remote Similarity	NPC229974
0.5924	Remote Similarity	NPC189068
0.5917	Remote Similarity	NPC242923
0.5902	Remote Similarity	NPC78941
0.5902	Remote Similarity	NPC282458
0.5892	Remote Similarity	NPC309832
0.5892	Remote Similarity	NPC219313
0.5887	Remote Similarity	NPC158055
0.587	Remote Similarity	NPC21448
0.587	Remote Similarity	NPC156461
0.587	Remote Similarity	NPC107374
0.585	Remote Similarity	NPC189261
0.5842	Remote Similarity	NPC469975
0.5841	Remote Similarity	NPC130570
0.5838	Remote Similarity	NPC290959
0.5838	Remote Similarity	NPC164665
0.5829	Remote Similarity	NPC136349
0.582	Remote Similarity	NPC150447
0.5818	Remote Similarity	NPC471603
0.5813	Remote Similarity	NPC87981
0.5813	Remote Similarity	NPC174114
0.5806	Remote Similarity	NPC269827
0.5804	Remote Similarity	NPC308906
0.5775	Remote Similarity	NPC121222
0.5767	Remote Similarity	NPC161224
0.5761	Remote Similarity	NPC8590
0.5758	Remote Similarity	NPC21461
0.5751	Remote Similarity	NPC195140
0.5745	Remote Similarity	NPC30540
0.574	Remote Similarity	NPC472027
0.5737	Remote Similarity	NPC207633
0.5737	Remote Similarity	NPC328479
0.5735	Remote Similarity	NPC280638
0.5728	Remote Similarity	NPC265576
0.5721	Remote Similarity	NPC473757
0.5714	Remote Similarity	NPC323091
0.5708	Remote Similarity	NPC71238
0.5707	Remote Similarity	NPC302778
0.5707	Remote Similarity	NPC212551
0.5706	Remote Similarity	NPC476564
0.5701	Remote Similarity	NPC54981
0.5696	Remote Similarity	NPC107160
0.5684	Remote Similarity	NPC185991
0.5684	Remote Similarity	NPC85689
0.5684	Remote Similarity	NPC211025
0.5677	Remote Similarity	NPC174802
0.5674	Remote Similarity	NPC104011
0.5661	Remote Similarity	NPC472031
0.5661	Remote Similarity	NPC472067
0.5661	Remote Similarity	NPC472066
0.5654	Remote Similarity	NPC472816
0.5654	Remote Similarity	NPC321814
0.565	Remote Similarity	NPC282247
0.5648	Remote Similarity	NPC469308
0.5648	Remote Similarity	NPC54537
0.5648	Remote Similarity	NPC224076
0.5646	Remote Similarity	NPC472289
0.5644	Remote Similarity	NPC12100
0.5625	Remote Similarity	NPC164952
0.5625	Remote Similarity	NPC130586
0.5619	Remote Similarity	NPC226245
0.5616	Remote Similarity	NPC475288
0.5614	Remote Similarity	NPC471506
0.5614	Remote Similarity	NPC17305
0.5613	Remote Similarity	NPC198673
0.5604	Remote Similarity	NPC284678

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 NPC473585 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	582
0.2-0.3	1741
0.3-0.4	3407
0.4-0.5	2115
0.5-0.6	1035
0.6-0.7	49
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6686	Remote Similarity	NPD171	Discontinued
0.6683	Remote Similarity	NPD7323	Phase 2
0.6667	Remote Similarity	NPD6619	Phase 3
0.6633	Remote Similarity	NPD7138	Phase 2
0.663	Remote Similarity	NPD516	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD8004	Discontinued
0.6591	Remote Similarity	NPD7158	Phase 1
0.657	Remote Similarity	NPD2450	Phase 2
0.657	Remote Similarity	NPD2452	Phase 2
0.657	Remote Similarity	NPD2451	Phase 2
0.657	Remote Similarity	NPD2453	Phase 2
0.6557	Remote Similarity	NPD5079	Phase 2
0.6553	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.655	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD5703	Discontinued
0.6526	Remote Similarity	NPD5080	Phase 2
0.6512	Remote Similarity	NPD3590	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7722	Suspended
0.6497	Remote Similarity	NPD5684	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5682	Phase 3
0.6497	Remote Similarity	NPD5683	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD4612	Discontinued
0.6422	Remote Similarity	NPD6849	Phase 2
0.6422	Remote Similarity	NPD6850	Phase 2
0.6414	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD2647	Phase 3
0.6364	Remote Similarity	NPD2876	Phase 3
0.6364	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4240	Approved
0.6316	Remote Similarity	NPD7103	Approved
0.6313	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD2824	Phase 2
0.63	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD6992	Phase 2
0.6262	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD2902	Phase 2
0.625	Remote Similarity	NPD2591	Phase 2
0.6244	Remote Similarity	NPD4990	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7935	Phase 2
0.6244	Remote Similarity	NPD5072	Discontinued
0.6244	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.623	Remote Similarity	NPD1313	Approved
0.621	Remote Similarity	NPD5827	Discontinued
0.6207	Remote Similarity	NPD1058	Discontinued
0.6199	Remote Similarity	NPD870	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4306	Phase 1
0.619	Remote Similarity	NPD4713	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4715	Clinical (unspecified phase)
0.619	Remote Similarity	NPD34	Approved
0.619	Remote Similarity	NPD4714	Approved
0.618	Remote Similarity	NPD3696	Approved
0.618	Remote Similarity	NPD3695	Approved
0.6175	Remote Similarity	NPD6772	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD4902	Discontinued
0.6167	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7857	Phase 3
0.6147	Remote Similarity	NPD7856	Phase 2
0.6146	Remote Similarity	NPD8120	Approved
0.6146	Remote Similarity	NPD1333	Phase 3
0.6146	Remote Similarity	NPD8121	Phase 3
0.6143	Remote Similarity	NPD6352	Phase 2
0.6143	Remote Similarity	NPD5486	Discontinued
0.6142	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD3708	Phase 2
0.6139	Remote Similarity	NPD3501	Phase 2
0.6129	Remote Similarity	NPD6528	Phase 1
0.6128	Remote Similarity	NPD7850	Discontinued
0.6128	Remote Similarity	NPD7851	Phase 1
0.6127	Remote Similarity	NPD7709	Discontinued
0.6127	Remote Similarity	NPD248	Discontinued
0.6111	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3430	Approved
0.6098	Remote Similarity	NPD3431	Approved
0.6098	Remote Similarity	NPD4615	Phase 2
0.6095	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4458	Phase 2
0.6091	Remote Similarity	NPD5843	Discontinued
0.6089	Remote Similarity	NPD6721	Phase 1
0.6082	Remote Similarity	NPD9408	Phase 3
0.608	Remote Similarity	NPD5962	Phase 2
0.608	Remote Similarity	NPD4763	Clinical (unspecified phase)
0.608	Remote Similarity	NPD4716	Approved
0.6073	Remote Similarity	NPD7423	Phase 2
0.607	Remote Similarity	NPD2456	Phase 2
0.607	Remote Similarity	NPD2457	Phase 2
0.6069	Remote Similarity	NPD9633	Phase 3
0.6062	Remote Similarity	NPD7988	Suspended
0.6056	Remote Similarity	NPD5458	Discontinued
0.6055	Remote Similarity	NPD7188	Phase 3
0.605	Remote Similarity	NPD4744	Clinical (unspecified phase)
0.605	Remote Similarity	NPD2526	Phase 2
0.605	Remote Similarity	NPD2523	Phase 2
0.6047	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7409	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD3107	Discontinued
0.6042	Remote Similarity	NPD1016	Phase 2
0.6042	Remote Similarity	NPD1015	Phase 2
0.6032	Remote Similarity	NPD546	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD5969	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD2646	Discontinued
0.6031	Remote Similarity	NPD1215	Discontinued
0.603	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD6957	Approved
0.6027	Remote Similarity	NPD3938	Phase 1
0.6027	Remote Similarity	NPD6643	Discontinued
0.6027	Remote Similarity	NPD6711	Approved
0.6027	Remote Similarity	NPD6958	Approved
0.6019	Remote Similarity	NPD4142	Discontinued
0.6017	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.601	Remote Similarity	NPD5757	Discontinued
0.6009	Remote Similarity	NPD7276	Approved
0.6009	Remote Similarity	NPD7277	Approved
0.6009	Remote Similarity	NPD5679	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5529	Phase 1
0.6	Remote Similarity	NPD7471	Discontinued
0.6	Remote Similarity	NPD193	Suspended
0.6	Remote Similarity	NPD5508	Phase 1
0.6	Remote Similarity	NPD2333	Discontinued
0.6	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD6129	Phase 2
0.599	Remote Similarity	NPD966	Clinical (unspecified phase)
0.599	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6572	Phase 2
0.5983	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6573	Phase 3
0.5981	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD6470	Phase 3
0.5972	Remote Similarity	NPD6816	Phase 3
0.5971	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD1286	Suspended
0.5969	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4352	Phase 1
0.596	Remote Similarity	NPD7297	Phase 2
0.596	Remote Similarity	NPD5666	Phase 2
0.5957	Remote Similarity	NPD6970	Phase 2
0.5953	Remote Similarity	NPD1197	Approved
0.5952	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6469	Phase 3
0.5952	Remote Similarity	NPD3287	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD7504	Discontinued
0.5948	Remote Similarity	NPD3849	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD185	Approved
0.5931	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7051	Phase 3
0.5929	Remote Similarity	NPD1273	Discontinued
0.5928	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD8257	Approved
0.5928	Remote Similarity	NPD8256	Approved
0.5926	Remote Similarity	NPD6520	Phase 3
0.5926	Remote Similarity	NPD6521	Phase 3
0.5919	Remote Similarity	NPD6856	Discontinued
0.5919	Remote Similarity	NPD5884	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD3265	Phase 1
0.5915	Remote Similarity	NPD2807	Discontinued
0.5909	Remote Similarity	NPD5996	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD8250	Phase 2
0.59	Remote Similarity	NPD7111	Discontinued
0.59	Remote Similarity	NPD3041	Approved
0.5899	Remote Similarity	NPD3860	Discontinued
0.5897	Remote Similarity	NPD705	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD5584	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD3906	Approved
0.5891	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.589	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.589	Remote Similarity	NPD6202	Discontinued
0.5888	Remote Similarity	NPD2364	Suspended
0.5887	Remote Similarity	NPD6840	Approved
0.5882	Remote Similarity	NPD4568	Phase 2
0.5882	Remote Similarity	NPD7397	Approved
0.5882	Remote Similarity	NPD7398	Approved
0.588	Remote Similarity	NPD7445	Phase 1
0.5877	Remote Similarity	NPD5885	Approved
0.5876	Remote Similarity	NPD2480	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD8105	Discontinued
0.5872	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD3013	Phase 3
0.5872	Remote Similarity	NPD6192	Phase 3
0.5871	Remote Similarity	NPD3432	Approved
0.587	Remote Similarity	NPD250	Approved
0.587	Remote Similarity	NPD249	Approved
0.587	Remote Similarity	NPD166	Approved
0.5869	Remote Similarity	NPD3831	Approved
0.5869	Remote Similarity	NPD6307	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD4213	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD6794	Approved
0.5864	Remote Similarity	NPD3405	Phase 3
0.5864	Remote Similarity	NPD2624	Phase 2
0.5864	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.5861	Remote Similarity	NPD5116	Phase 1
0.586	Remote Similarity	NPD1915	Phase 1
0.5857	Remote Similarity	NPD3362	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5465	Phase 2
0.5856	Remote Similarity	NPD4893	Phase 3
0.5854	Remote Similarity	NPD7757	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