NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	454.38
Volume:	514.257
LogP:	6.494
LogD:	5.422
LogS:	-5.622
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	4.95
Fsp3:	0.903
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.135
MDCK Permeability:	9.97E-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.791
Plasma Protein Binding (PPB):	89.01%
Volume Distribution (VD):	1.205
Pgp-substrate:	2.13%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.237
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.197
CYP2C9-substrate:	0.098
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.239
CYP3A4-inhibitor:	0.841
CYP3A4-substrate:	0.673

ADMET: Excretion

Clearance (CL):	5.957
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.223
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.887
Carcinogencity:	0.027
Eye Corrosion:	0.813
Eye Irritation:	0.638
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: NPC477579

Natural Product ID:	NPC477579
*Common Name:**	2-[(1S,2R,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picen-4a-yl]acetaldehyde
IUPAC Name:	2-[(1S,2R,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picen-4a-yl]acetaldehyde
Synonyms:
Standard InCHIKey:	XVYNHNJCVHARPC-JFEQRZBLSA-N
Standard InCHI:	InChI=1S/C31H50O2/c1-20-10-15-31(18-19-32)17-16-29(6)22(26(31)21(20)2)8-9-24-28(5)13-12-25(33)27(3,4)23(28)11-14-30(24,29)7/h8,19-21,23-26,33H,9-18H2,1-7H3/t20-,21+,23+,24-,25+,26+,28+,29-,30-,31-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)CC=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44583866
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	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	5

Activity Type	# Activity
Cell Line	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	85400	nM	PMID[16933868]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	158000	nM	PMID[16933868]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	205000	nM	PMID[16933868]
NPT27	Others	Unspecified		IC50	=	94700	nM	PMID[16933868]
NPT2	Others	Unspecified		IC50	=	99000	nM	PMID[16933868]

☑ 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 NPC477579 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	199
0.1-0.2	1397
0.2-0.3	5540
0.3-0.4	16265
0.4-0.5	7884
0.5-0.6	5032
0.6-0.7	4428
0.7-0.8	1473
0.8-0.85	178
0.85-0.9	183
0.9-0.95	110
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC95594
1.0	High Similarity	NPC235341
0.963	High Similarity	NPC133954
0.9512	High Similarity	NPC475862
0.9512	High Similarity	NPC74363
0.9512	High Similarity	NPC213412
0.9398	High Similarity	NPC142415
0.9398	High Similarity	NPC307426
0.9398	High Similarity	NPC102683
0.9398	High Similarity	NPC242468
0.9398	High Similarity	NPC171203
0.9398	High Similarity	NPC68160
0.9398	High Similarity	NPC18064
0.9398	High Similarity	NPC293564
0.9398	High Similarity	NPC98442
0.9398	High Similarity	NPC73064
0.9398	High Similarity	NPC130577
0.9398	High Similarity	NPC88716
0.9398	High Similarity	NPC51700
0.9302	High Similarity	NPC298554
0.9286	High Similarity	NPC246708
0.9286	High Similarity	NPC473242
0.9286	High Similarity	NPC470629
0.9286	High Similarity	NPC290690
0.9286	High Similarity	NPC182797
0.9286	High Similarity	NPC40552
0.9286	High Similarity	NPC52169
0.9286	High Similarity	NPC181225
0.9286	High Similarity	NPC474512
0.9286	High Similarity	NPC206060
0.9286	High Similarity	NPC17733
0.9277	High Similarity	NPC72638
0.9268	High Similarity	NPC180834
0.9195	High Similarity	NPC222047
0.9195	High Similarity	NPC209868
0.9176	High Similarity	NPC121798
0.9176	High Similarity	NPC263393
0.9176	High Similarity	NPC274330
0.9176	High Similarity	NPC474972
0.9176	High Similarity	NPC470588
0.9176	High Similarity	NPC95246
0.9176	High Similarity	NPC143232
0.9176	High Similarity	NPC25906
0.9176	High Similarity	NPC130520
0.9176	High Similarity	NPC61543
0.9176	High Similarity	NPC293048
0.9176	High Similarity	NPC225585
0.9176	High Similarity	NPC234346
0.9176	High Similarity	NPC69627
0.9176	High Similarity	NPC290972
0.9176	High Similarity	NPC59263
0.9176	High Similarity	NPC161751
0.9176	High Similarity	NPC270768
0.9176	High Similarity	NPC198664
0.9176	High Similarity	NPC127689
0.9176	High Similarity	NPC64872
0.9136	High Similarity	NPC3915
0.907	High Similarity	NPC130278
0.907	High Similarity	NPC290614
0.907	High Similarity	NPC111110
0.907	High Similarity	NPC7260
0.907	High Similarity	NPC227467
0.907	High Similarity	NPC18872
0.907	High Similarity	NPC291028
0.907	High Similarity	NPC120968
0.907	High Similarity	NPC470589
0.907	High Similarity	NPC477872
0.907	High Similarity	NPC172361
0.907	High Similarity	NPC273621
0.907	High Similarity	NPC210037
0.907	High Similarity	NPC86372
0.907	High Similarity	NPC126369
0.9059	High Similarity	NPC474925
0.9024	High Similarity	NPC163236
0.9024	High Similarity	NPC310989
0.8966	High Similarity	NPC25299
0.8966	High Similarity	NPC306541
0.8966	High Similarity	NPC300351
0.8966	High Similarity	NPC84319
0.8966	High Similarity	NPC472149
0.8966	High Similarity	NPC235884
0.8966	High Similarity	NPC155120
0.8966	High Similarity	NPC105189
0.8966	High Similarity	NPC4036
0.8966	High Similarity	NPC324341
0.8966	High Similarity	NPC145067
0.8966	High Similarity	NPC288833
0.8966	High Similarity	NPC474525
0.8966	High Similarity	NPC966
0.8966	High Similarity	NPC65120
0.8966	High Similarity	NPC228784
0.8966	High Similarity	NPC282616
0.8966	High Similarity	NPC158030
0.8966	High Similarity	NPC71074
0.8966	High Similarity	NPC187722
0.8966	High Similarity	NPC233455
0.8966	High Similarity	NPC52021
0.8953	High Similarity	NPC474686
0.8941	High Similarity	NPC71507
0.8929	High Similarity	NPC274724
0.8889	High Similarity	NPC187933
0.8875	High Similarity	NPC34177
0.8875	High Similarity	NPC157996
0.8875	High Similarity	NPC40394
0.8875	High Similarity	NPC101475
0.8864	High Similarity	NPC229281
0.8864	High Similarity	NPC63118
0.8864	High Similarity	NPC118519
0.8864	High Similarity	NPC136313
0.8864	High Similarity	NPC272075
0.8864	High Similarity	NPC307335
0.8864	High Similarity	NPC295643
0.8864	High Similarity	NPC275809
0.8864	High Similarity	NPC214756
0.8864	High Similarity	NPC49776
0.8864	High Similarity	NPC202728
0.8864	High Similarity	NPC158059
0.8864	High Similarity	NPC474436
0.8864	High Similarity	NPC86368
0.8864	High Similarity	NPC74855
0.8851	High Similarity	NPC474728
0.8851	High Similarity	NPC49320
0.8851	High Similarity	NPC120840
0.8851	High Similarity	NPC113989
0.8851	High Similarity	NPC46441
0.8851	High Similarity	NPC193750
0.8837	High Similarity	NPC224145
0.8837	High Similarity	NPC472802
0.8824	High Similarity	NPC94755
0.8824	High Similarity	NPC158393
0.881	High Similarity	NPC171789
0.881	High Similarity	NPC74595
0.881	High Similarity	NPC264665
0.8795	High Similarity	NPC48362
0.8791	High Similarity	NPC188833
0.8791	High Similarity	NPC471966
0.8765	High Similarity	NPC300499
0.8765	High Similarity	NPC474989
0.8765	High Similarity	NPC158662
0.8765	High Similarity	NPC470396
0.8765	High Similarity	NPC230295
0.8765	High Similarity	NPC22955
0.8765	High Similarity	NPC196753
0.8765	High Similarity	NPC99168
0.8765	High Similarity	NPC98386
0.8765	High Similarity	NPC253807
0.8764	High Similarity	NPC91010
0.8764	High Similarity	NPC299996
0.8764	High Similarity	NPC231063
0.8764	High Similarity	NPC145667
0.8764	High Similarity	NPC20235
0.8764	High Similarity	NPC282395
0.8764	High Similarity	NPC474529
0.8764	High Similarity	NPC32407
0.8764	High Similarity	NPC263548
0.8764	High Similarity	NPC88116
0.8764	High Similarity	NPC159365
0.8764	High Similarity	NPC6818
0.8764	High Similarity	NPC191412
0.8764	High Similarity	NPC114159
0.875	High Similarity	NPC60755
0.875	High Similarity	NPC265328
0.875	High Similarity	NPC120098
0.875	High Similarity	NPC285184
0.875	High Similarity	NPC6255
0.875	High Similarity	NPC301244
0.875	High Similarity	NPC471588
0.875	High Similarity	NPC290598
0.875	High Similarity	NPC470590
0.875	High Similarity	NPC27765
0.875	High Similarity	NPC475708
0.875	High Similarity	NPC77099
0.875	High Similarity	NPC38754
0.875	High Similarity	NPC30590
0.875	High Similarity	NPC122418
0.8736	High Similarity	NPC30522
0.869	High Similarity	NPC307258
0.8681	High Similarity	NPC21728
0.8667	High Similarity	NPC148523
0.8667	High Similarity	NPC474727
0.8667	High Similarity	NPC473240
0.8667	High Similarity	NPC139570
0.8667	High Similarity	NPC198245
0.8667	High Similarity	NPC96916
0.8659	High Similarity	NPC291379
0.8659	High Similarity	NPC53744
0.8652	High Similarity	NPC474806
0.8652	High Similarity	NPC118490
0.8652	High Similarity	NPC133579
0.8636	High Similarity	NPC85173
0.8625	High Similarity	NPC138374
0.8625	High Similarity	NPC34700
0.8621	High Similarity	NPC474474
0.8621	High Similarity	NPC230387
0.8605	High Similarity	NPC9892
0.8605	High Similarity	NPC10005
0.8605	High Similarity	NPC325594
0.8605	High Similarity	NPC269396
0.8605	High Similarity	NPC91525
0.8605	High Similarity	NPC98236

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 NPC477579 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1771
0.2-0.3	4087
0.3-0.4	2178
0.4-0.5	537
0.5-0.6	157
0.6-0.7	196
0.7-0.8	34
0.8-0.85	3
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8966	High Similarity	NPD7515	Phase 2
0.8659	High Similarity	NPD7645	Phase 2
0.8556	High Similarity	NPD7748	Approved
0.8391	Intermediate Similarity	NPD3618	Phase 1
0.8372	Intermediate Similarity	NPD4786	Approved
0.8353	Intermediate Similarity	NPD3667	Approved
0.8315	Intermediate Similarity	NPD5328	Approved
0.828	Intermediate Similarity	NPD7902	Approved
0.8276	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD6079	Approved
0.7979	Intermediate Similarity	NPD4697	Phase 3
0.7957	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD7900	Approved
0.7955	Intermediate Similarity	NPD3665	Phase 1
0.7955	Intermediate Similarity	NPD3666	Approved
0.7955	Intermediate Similarity	NPD3133	Approved
0.7849	Intermediate Similarity	NPD4202	Approved
0.7701	Intermediate Similarity	NPD7525	Registered
0.7604	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD5222	Approved
0.7604	Intermediate Similarity	NPD5221	Approved
0.7556	Intermediate Similarity	NPD3668	Phase 3
0.7553	Intermediate Similarity	NPD8035	Phase 2
0.7553	Intermediate Similarity	NPD8034	Phase 2
0.7529	Intermediate Similarity	NPD7339	Approved
0.7529	Intermediate Similarity	NPD6942	Approved
0.7526	Intermediate Similarity	NPD4755	Approved
0.7526	Intermediate Similarity	NPD5173	Approved
0.7474	Intermediate Similarity	NPD6399	Phase 3
0.7442	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5279	Phase 3
0.7374	Intermediate Similarity	NPD5286	Approved
0.7374	Intermediate Similarity	NPD4700	Approved
0.7374	Intermediate Similarity	NPD4696	Approved
0.7374	Intermediate Similarity	NPD5285	Approved
0.734	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4753	Phase 2
0.7333	Intermediate Similarity	NPD4221	Approved
0.7333	Intermediate Similarity	NPD4223	Phase 3
0.7303	Intermediate Similarity	NPD4695	Discontinued
0.73	Intermediate Similarity	NPD5223	Approved
0.7283	Intermediate Similarity	NPD5329	Approved
0.7273	Intermediate Similarity	NPD7638	Approved
0.7253	Intermediate Similarity	NPD4788	Approved
0.7228	Intermediate Similarity	NPD5226	Approved
0.7228	Intermediate Similarity	NPD5224	Approved
0.7228	Intermediate Similarity	NPD4633	Approved
0.7228	Intermediate Similarity	NPD5225	Approved
0.7228	Intermediate Similarity	NPD5211	Phase 2
0.7204	Intermediate Similarity	NPD7521	Approved
0.7204	Intermediate Similarity	NPD7334	Approved
0.7204	Intermediate Similarity	NPD6684	Approved
0.7204	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7146	Approved
0.7204	Intermediate Similarity	NPD6409	Approved
0.7204	Intermediate Similarity	NPD5330	Approved
0.72	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD7639	Approved
0.7184	Intermediate Similarity	NPD7128	Approved
0.7184	Intermediate Similarity	NPD6675	Approved
0.7184	Intermediate Similarity	NPD6402	Approved
0.7184	Intermediate Similarity	NPD5739	Approved
0.7176	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4197	Approved
0.7157	Intermediate Similarity	NPD5174	Approved
0.7157	Intermediate Similarity	NPD5175	Approved
0.7157	Intermediate Similarity	NPD4754	Approved
0.7143	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD3573	Approved
0.7087	Intermediate Similarity	NPD5141	Approved
0.7079	Intermediate Similarity	NPD3617	Approved
0.7053	Intermediate Similarity	NPD6903	Approved
0.7048	Intermediate Similarity	NPD7320	Approved
0.7048	Intermediate Similarity	NPD6881	Approved
0.7048	Intermediate Similarity	NPD6899	Approved
0.7045	Intermediate Similarity	NPD6117	Approved
0.7021	Intermediate Similarity	NPD4693	Phase 3
0.7021	Intermediate Similarity	NPD4690	Approved
0.7021	Intermediate Similarity	NPD4519	Discontinued
0.7021	Intermediate Similarity	NPD4138	Approved
0.7021	Intermediate Similarity	NPD4688	Approved
0.7021	Intermediate Similarity	NPD5205	Approved
0.7021	Intermediate Similarity	NPD4689	Approved
0.7021	Intermediate Similarity	NPD4623	Approved
0.7019	Intermediate Similarity	NPD4768	Approved
0.7019	Intermediate Similarity	NPD4767	Approved
0.7011	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6411	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.6981	Remote Similarity	NPD6372	Approved
0.6981	Remote Similarity	NPD6373	Approved
0.697	Remote Similarity	NPD4629	Approved
0.697	Remote Similarity	NPD5210	Approved
0.6966	Remote Similarity	NPD6116	Phase 1
0.6952	Remote Similarity	NPD5701	Approved
0.6952	Remote Similarity	NPD5697	Approved
0.6932	Remote Similarity	NPD3703	Phase 2
0.6916	Remote Similarity	NPD6883	Approved
0.6916	Remote Similarity	NPD7290	Approved
0.6916	Remote Similarity	NPD7102	Approved
0.69	Remote Similarity	NPD7614	Phase 1
0.6889	Remote Similarity	NPD6118	Approved
0.6889	Remote Similarity	NPD6115	Approved
0.6889	Remote Similarity	NPD6114	Approved
0.6889	Remote Similarity	NPD6697	Approved
0.6887	Remote Similarity	NPD4729	Approved
0.6887	Remote Similarity	NPD5168	Approved
0.6887	Remote Similarity	NPD6011	Approved
0.6887	Remote Similarity	NPD5128	Approved
0.6887	Remote Similarity	NPD4730	Approved
0.6875	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD5737	Approved
0.686	Remote Similarity	NPD4244	Approved
0.686	Remote Similarity	NPD4245	Approved
0.6852	Remote Similarity	NPD8130	Phase 1
0.6852	Remote Similarity	NPD6650	Approved
0.6852	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6617	Approved
0.6852	Remote Similarity	NPD6869	Approved
0.6852	Remote Similarity	NPD6649	Approved
0.6852	Remote Similarity	NPD6847	Approved
0.6842	Remote Similarity	NPD5690	Phase 2
0.6842	Remote Similarity	NPD5280	Approved
0.6842	Remote Similarity	NPD4694	Approved
0.6822	Remote Similarity	NPD6013	Approved
0.6822	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6014	Approved
0.6822	Remote Similarity	NPD6012	Approved
0.6818	Remote Similarity	NPD6926	Approved
0.6818	Remote Similarity	NPD6924	Approved
0.6804	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6101	Approved
0.6792	Remote Similarity	NPD6412	Phase 2
0.6789	Remote Similarity	NPD6882	Approved
0.6789	Remote Similarity	NPD8297	Approved
0.6783	Remote Similarity	NPD8328	Phase 3
0.6782	Remote Similarity	NPD4243	Approved
0.6759	Remote Similarity	NPD5249	Phase 3
0.6759	Remote Similarity	NPD4634	Approved
0.6759	Remote Similarity	NPD5247	Approved
0.6759	Remote Similarity	NPD5169	Approved
0.6759	Remote Similarity	NPD5135	Approved
0.6759	Remote Similarity	NPD5250	Approved
0.6759	Remote Similarity	NPD5251	Approved
0.6759	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5248	Approved
0.6744	Remote Similarity	NPD3698	Phase 2
0.6744	Remote Similarity	NPD4137	Phase 3
0.6742	Remote Similarity	NPD8264	Approved
0.6739	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5217	Approved
0.6697	Remote Similarity	NPD5215	Approved
0.6697	Remote Similarity	NPD5216	Approved
0.6697	Remote Similarity	NPD5127	Approved
0.6696	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD4747	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD4691	Approved
0.6634	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5695	Phase 3
0.663	Remote Similarity	NPD4195	Approved
0.6629	Remote Similarity	NPD4784	Approved
0.6629	Remote Similarity	NPD4785	Approved
0.6628	Remote Similarity	NPD5360	Phase 3
0.6628	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6868	Approved
0.6602	Remote Similarity	NPD5696	Approved
0.6602	Remote Similarity	NPD5290	Discontinued
0.6598	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7150	Approved
0.6591	Remote Similarity	NPD7152	Approved
0.6591	Remote Similarity	NPD7151	Approved
0.6577	Remote Similarity	NPD4632	Approved
0.6571	Remote Similarity	NPD7632	Discontinued
0.6569	Remote Similarity	NPD7732	Phase 3
0.6559	Remote Similarity	NPD4748	Discontinued
0.6559	Remote Similarity	NPD7509	Discontinued
0.6552	Remote Similarity	NPD6922	Approved
0.6552	Remote Similarity	NPD6923	Approved
0.6525	Remote Similarity	NPD7507	Approved
0.6522	Remote Similarity	NPD3671	Phase 1
0.6518	Remote Similarity	NPD5167	Approved
0.65	Remote Similarity	NPD5281	Approved
0.65	Remote Similarity	NPD5284	Approved
0.6491	Remote Similarity	NPD6335	Approved
0.6489	Remote Similarity	NPD8028	Phase 2
0.6477	Remote Similarity	NPD7144	Approved
0.6477	Remote Similarity	NPD7143	Approved
0.6471	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6904	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