NPASS Compound

Structure

CID326753 OpenBabel06191716192D 31 32 0 0 1 0 0 0 0 0999 V2000 7.6619 7.8466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7007 0.3890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5573 6.8521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6438 6.4454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5393 5.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6257 5.0441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5212 4.0496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6077 3.6429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5031 2.6483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5896 2.2416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4851 1.2471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5715 0.8403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4670 -0.1542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5534 -0.5609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7444 0.0269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8489 1.0214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8736 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0399 1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.7026 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1445 2.6037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7872 0.7957 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 3 1 0 0 0 0 2 30 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 25 1 0 0 0 0 17 19 2 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 25 1 0 0 0 0 23 27 1 0 0 0 0 24 28 2 0 0 0 0 25 29 1 6 0 0 0 26 31 1 0 0 0 0 27 30 1 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.34
Volume:	485.687
LogP:	7.085
LogD:	4.565
LogS:	-6.531
# Rotatable Bonds:	17
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.256
Synthetic Accessibility Score:	4.363
Fsp3:	0.815
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.795
MDCK Permeability:	2.4244276573881507e-05
Pgp-inhibitor:	0.411
Pgp-substrate:	0.328
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.184
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	99.44510650634766%
Volume Distribution (VD):	1.706
Pgp-substrate:	1.2655295133590698%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.586
CYP2C19-inhibitor:	0.587
CYP2C19-substrate:	0.822
CYP2C9-inhibitor:	0.302
CYP2C9-substrate:	0.742
CYP2D6-inhibitor:	0.914
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.685
CYP3A4-substrate:	0.512

ADMET: Excretion

Clearance (CL):	9.099
Half-life (T1/2):	0.187

ADMET: Toxicity

hERG Blockers:	0.401
Human Hepatotoxicity (H-HT):	0.453
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.984
Carcinogencity:	0.791
Eye Corrosion:	0.07
Eye Irritation:	0.802
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC326753

Natural Product ID:	NPC326753
*Common Name:**	2-[(2R)-2-Hydroxyheptadecyl]-2-Methoxy-1-Oxaspiro[4.5]Deca-6,9-Dien-8-One
IUPAC Name:	2-[(2R)-2-hydroxyheptadecyl]-2-methoxy-1-oxaspiro[4.5]deca-6,9-dien-8-one
Synonyms:
Standard InCHIKey:	LOBKLUVDTHVJSR-CSMDKSQMSA-N
Standard InCHI:	InChI=1S/C27H46O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-25(29)23-27(30-2)22-21-26(31-27)19-17-24(28)18-20-26/h17-20,25,29H,3-16,21-23H2,1-2H3/t25-,27?/m1/s1
SMILES:	CCCCCCCCCCCCCCCC(CC1(CCC2(O1)C=CC(=O)C=C2)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255879
PubChem CID:	44448222
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002951] Long-chain fatty alcohols

*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
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	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
ED50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	0.5	uM	PMID[514573]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	0.9	uM	PMID[514574]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	0.9	uM	PMID[514573]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	0.7	uM	PMID[514574]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	0.7	uM	PMID[514573]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	0.9	uM	PMID[514574]

☑ 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 NPC326753 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	150
0.1-0.2	1256
0.2-0.3	6070
0.3-0.4	16419
0.4-0.5	9531
0.5-0.6	6967
0.6-0.7	2198
0.7-0.8	98
0.8-0.85	2
0.85-0.9	0
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9351	High Similarity	NPC27314
0.9351	High Similarity	NPC31019
0.9351	High Similarity	NPC2379
0.9351	High Similarity	NPC263087
0.9351	High Similarity	NPC106912
0.8608	High Similarity	NPC471552
0.8608	High Similarity	NPC473339
0.814	Intermediate Similarity	NPC471569
0.8	Intermediate Similarity	NPC266842
0.7976	Intermediate Similarity	NPC473353
0.7738	Intermediate Similarity	NPC474809
0.7683	Intermediate Similarity	NPC139712
0.7667	Intermediate Similarity	NPC256368
0.7647	Intermediate Similarity	NPC471301
0.7619	Intermediate Similarity	NPC471298
0.7614	Intermediate Similarity	NPC471054
0.7556	Intermediate Similarity	NPC475098
0.7556	Intermediate Similarity	NPC189651
0.7529	Intermediate Similarity	NPC471297
0.75	Intermediate Similarity	NPC474280
0.75	Intermediate Similarity	NPC112868
0.75	Intermediate Similarity	NPC475944
0.75	Intermediate Similarity	NPC106051
0.7471	Intermediate Similarity	NPC311163
0.7439	Intermediate Similarity	NPC474278
0.7416	Intermediate Similarity	NPC133450
0.7412	Intermediate Similarity	NPC474252
0.7412	Intermediate Similarity	NPC323251
0.7391	Intermediate Similarity	NPC13924
0.7386	Intermediate Similarity	NPC313658
0.7386	Intermediate Similarity	NPC241054
0.7386	Intermediate Similarity	NPC300779
0.7386	Intermediate Similarity	NPC316138
0.7375	Intermediate Similarity	NPC327383
0.7375	Intermediate Similarity	NPC185186
0.7356	Intermediate Similarity	NPC163606
0.7356	Intermediate Similarity	NPC471494
0.7349	Intermediate Similarity	NPC474816
0.7349	Intermediate Similarity	NPC209135
0.734	Intermediate Similarity	NPC203627
0.7333	Intermediate Similarity	NPC177668
0.7333	Intermediate Similarity	NPC202886
0.7317	Intermediate Similarity	NPC477202
0.7317	Intermediate Similarity	NPC469880
0.7303	Intermediate Similarity	NPC472011
0.7303	Intermediate Similarity	NPC472378
0.7294	Intermediate Similarity	NPC469469
0.7294	Intermediate Similarity	NPC184208
0.7294	Intermediate Similarity	NPC8538
0.7294	Intermediate Similarity	NPC315731
0.7284	Intermediate Similarity	NPC144995
0.7284	Intermediate Similarity	NPC227814
0.7283	Intermediate Similarity	NPC470521
0.7262	Intermediate Similarity	NPC475210
0.7262	Intermediate Similarity	NPC226226
0.7262	Intermediate Similarity	NPC55304
0.7253	Intermediate Similarity	NPC470520
0.7253	Intermediate Similarity	NPC477749
0.7253	Intermediate Similarity	NPC472010
0.7241	Intermediate Similarity	NPC471302
0.7241	Intermediate Similarity	NPC266718
0.7241	Intermediate Similarity	NPC126518
0.7241	Intermediate Similarity	NPC475035
0.7229	Intermediate Similarity	NPC477203
0.7229	Intermediate Similarity	NPC262747
0.7222	Intermediate Similarity	NPC477748
0.7216	Intermediate Similarity	NPC473070
0.7215	Intermediate Similarity	NPC101622
0.7209	Intermediate Similarity	NPC475690
0.7195	Intermediate Similarity	NPC285840
0.7195	Intermediate Similarity	NPC327041
0.7174	Intermediate Similarity	NPC156553
0.7174	Intermediate Similarity	NPC59646
0.7174	Intermediate Similarity	NPC238090
0.7174	Intermediate Similarity	NPC472196
0.7174	Intermediate Similarity	NPC472195
0.716	Intermediate Similarity	NPC329914
0.716	Intermediate Similarity	NPC329890
0.7159	Intermediate Similarity	NPC11804
0.7143	Intermediate Similarity	NPC473448
0.7143	Intermediate Similarity	NPC3436
0.7143	Intermediate Similarity	NPC248775
0.7143	Intermediate Similarity	NPC473068
0.7143	Intermediate Similarity	NPC231739
0.7126	Intermediate Similarity	NPC229799
0.7126	Intermediate Similarity	NPC44261
0.7126	Intermediate Similarity	NPC286770
0.7126	Intermediate Similarity	NPC161045
0.7126	Intermediate Similarity	NPC284472
0.7125	Intermediate Similarity	NPC4299
0.7113	Intermediate Similarity	NPC150463
0.7111	Intermediate Similarity	NPC60765
0.71	Intermediate Similarity	NPC473069
0.7097	Intermediate Similarity	NPC159698
0.7093	Intermediate Similarity	NPC246621
0.7083	Intermediate Similarity	NPC472012
0.7079	Intermediate Similarity	NPC208473
0.7079	Intermediate Similarity	NPC475461
0.7079	Intermediate Similarity	NPC305475
0.7073	Intermediate Similarity	NPC160540
0.7065	Intermediate Similarity	NPC32494
0.7065	Intermediate Similarity	NPC175842
0.7059	Intermediate Similarity	NPC180725
0.7059	Intermediate Similarity	NPC470149
0.7059	Intermediate Similarity	NPC473981
0.7059	Intermediate Similarity	NPC470148
0.7059	Intermediate Similarity	NPC473980
0.7051	Intermediate Similarity	NPC137163
0.7045	Intermediate Similarity	NPC31086
0.7045	Intermediate Similarity	NPC474865
0.7045	Intermediate Similarity	NPC96259
0.7045	Intermediate Similarity	NPC141193
0.7045	Intermediate Similarity	NPC186155
0.7045	Intermediate Similarity	NPC78673
0.7045	Intermediate Similarity	NPC160517
0.7041	Intermediate Similarity	NPC472747
0.7041	Intermediate Similarity	NPC472750
0.7037	Intermediate Similarity	NPC316185
0.7033	Intermediate Similarity	NPC470734
0.7033	Intermediate Similarity	NPC225283
0.7033	Intermediate Similarity	NPC295448
0.7024	Intermediate Similarity	NPC474026
0.7024	Intermediate Similarity	NPC473756
0.7024	Intermediate Similarity	NPC476439
0.7024	Intermediate Similarity	NPC233071
0.7011	Intermediate Similarity	NPC11383
0.7011	Intermediate Similarity	NPC310450
0.7011	Intermediate Similarity	NPC475046
0.7011	Intermediate Similarity	NPC474959
0.7011	Intermediate Similarity	NPC324170
0.7	Intermediate Similarity	NPC471055
0.7	Intermediate Similarity	NPC475037
0.7	Intermediate Similarity	NPC72513
0.7	Intermediate Similarity	NPC109376
0.7	Intermediate Similarity	NPC471056
0.7	Intermediate Similarity	NPC472947
0.7	Intermediate Similarity	NPC199382
0.7	Intermediate Similarity	NPC151481
0.6989	Remote Similarity	NPC471483
0.6988	Remote Similarity	NPC329852
0.6979	Remote Similarity	NPC473154
0.6977	Remote Similarity	NPC470147
0.6977	Remote Similarity	NPC133226
0.6974	Remote Similarity	NPC26810
0.697	Remote Similarity	NPC472748
0.6966	Remote Similarity	NPC165162
0.6966	Remote Similarity	NPC474860
0.6966	Remote Similarity	NPC261380
0.6966	Remote Similarity	NPC255307
0.6966	Remote Similarity	NPC471300
0.6966	Remote Similarity	NPC475034
0.6962	Remote Similarity	NPC472266
0.6957	Remote Similarity	NPC144133
0.6957	Remote Similarity	NPC475855
0.6957	Remote Similarity	NPC118078
0.6957	Remote Similarity	NPC3952
0.6957	Remote Similarity	NPC469403
0.6957	Remote Similarity	NPC179394
0.6951	Remote Similarity	NPC222244
0.6951	Remote Similarity	NPC16349
0.6947	Remote Similarity	NPC288350
0.6947	Remote Similarity	NPC173329
0.6941	Remote Similarity	NPC475699
0.6941	Remote Similarity	NPC192006
0.6932	Remote Similarity	NPC169575
0.6932	Remote Similarity	NPC477785
0.6932	Remote Similarity	NPC40746
0.6932	Remote Similarity	NPC16488
0.6932	Remote Similarity	NPC477784
0.6932	Remote Similarity	NPC477786
0.6931	Remote Similarity	NPC470024
0.6931	Remote Similarity	NPC224660
0.6923	Remote Similarity	NPC472810
0.6923	Remote Similarity	NPC472809
0.6923	Remote Similarity	NPC477302
0.6915	Remote Similarity	NPC469491
0.6915	Remote Similarity	NPC475572
0.6915	Remote Similarity	NPC104925
0.6915	Remote Similarity	NPC474338
0.6915	Remote Similarity	NPC298973
0.6914	Remote Similarity	NPC469660
0.6914	Remote Similarity	NPC476037
0.6914	Remote Similarity	NPC476012
0.6905	Remote Similarity	NPC229655
0.6905	Remote Similarity	NPC188860
0.69	Remote Similarity	NPC472751
0.69	Remote Similarity	NPC172867
0.69	Remote Similarity	NPC239961
0.69	Remote Similarity	NPC472749
0.69	Remote Similarity	NPC218158
0.6897	Remote Similarity	NPC474894
0.6889	Remote Similarity	NPC61527
0.6889	Remote Similarity	NPC477015
0.6889	Remote Similarity	NPC469483
0.6889	Remote Similarity	NPC150755
0.6882	Remote Similarity	NPC141831
0.6875	Remote Similarity	NPC91695
0.6875	Remote Similarity	NPC98112
0.6875	Remote Similarity	NPC475760
0.6875	Remote Similarity	NPC70145

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 NPC326753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	1879
0.2-0.3	4214
0.3-0.4	2190
0.4-0.5	415
0.5-0.6	285
0.6-0.7	31
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
0.7241	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7838	Discovery
0.6709	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD46	Approved
0.6596	Remote Similarity	NPD6698	Approved
0.6596	Remote Similarity	NPD5785	Approved
0.6591	Remote Similarity	NPD4822	Approved
0.6591	Remote Similarity	NPD4819	Approved
0.6591	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4821	Approved
0.6591	Remote Similarity	NPD4820	Approved
0.65	Remote Similarity	NPD5344	Discontinued
0.6495	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6435	Approved
0.6442	Remote Similarity	NPD6686	Approved
0.6413	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5363	Approved
0.6413	Remote Similarity	NPD1694	Approved
0.6374	Remote Similarity	NPD7154	Phase 3
0.6364	Remote Similarity	NPD4268	Approved
0.6364	Remote Similarity	NPD4271	Approved
0.63	Remote Similarity	NPD4225	Approved
0.6277	Remote Similarity	NPD4250	Approved
0.6277	Remote Similarity	NPD4251	Approved
0.6262	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6648	Approved
0.6222	Remote Similarity	NPD5368	Approved
0.622	Remote Similarity	NPD7331	Phase 2
0.6204	Remote Similarity	NPD6882	Approved
0.6195	Remote Similarity	NPD7503	Approved
0.618	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4249	Approved
0.6154	Remote Similarity	NPD5369	Approved
0.6125	Remote Similarity	NPD368	Approved
0.6087	Remote Similarity	NPD4270	Approved
0.6087	Remote Similarity	NPD4269	Approved
0.6087	Remote Similarity	NPD5209	Approved
0.6061	Remote Similarity	NPD5282	Discontinued
0.6038	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6412	Phase 2
0.6023	Remote Similarity	NPD8039	Approved
0.6022	Remote Similarity	NPD5362	Discontinued
0.6019	Remote Similarity	NPD6371	Approved
0.6	Remote Similarity	NPD5786	Approved
0.5982	Remote Similarity	NPD7115	Discovery
0.5981	Remote Similarity	NPD6881	Approved
0.5981	Remote Similarity	NPD6899	Approved
0.598	Remote Similarity	NPD7638	Approved
0.5976	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6054	Approved
0.5963	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5779	Approved
0.596	Remote Similarity	NPD5778	Approved
0.5957	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD7642	Approved
0.5943	Remote Similarity	NPD4211	Phase 1
0.5941	Remote Similarity	NPD7839	Suspended
0.5929	Remote Similarity	NPD7327	Approved
0.5929	Remote Similarity	NPD7328	Approved
0.5922	Remote Similarity	NPD7640	Approved
0.5922	Remote Similarity	NPD7639	Approved
0.5914	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD8516	Approved
0.5913	Remote Similarity	NPD8517	Approved
0.5913	Remote Similarity	NPD8515	Approved
0.5913	Remote Similarity	NPD8513	Phase 3
0.5909	Remote Similarity	NPD6053	Discontinued
0.5904	Remote Similarity	NPD7341	Phase 2
0.5895	Remote Similarity	NPD1696	Phase 3
0.5889	Remote Similarity	NPD4756	Discovery
0.5888	Remote Similarity	NPD5697	Approved
0.5882	Remote Similarity	NPD6084	Phase 2
0.5882	Remote Similarity	NPD6083	Phase 2
0.5877	Remote Similarity	NPD7516	Approved
0.5872	Remote Similarity	NPD6883	Approved
0.5872	Remote Similarity	NPD7290	Approved
0.5872	Remote Similarity	NPD7102	Approved
0.587	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4252	Approved
0.5862	Remote Similarity	NPD6370	Approved
0.5859	Remote Similarity	NPD7637	Suspended
0.5859	Remote Similarity	NPD7983	Approved
0.5854	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD5332	Approved
0.5851	Remote Similarity	NPD5331	Approved
0.5851	Remote Similarity	NPD6695	Phase 3
0.5833	Remote Similarity	NPD3704	Approved
0.5826	Remote Similarity	NPD8294	Approved
0.5826	Remote Similarity	NPD8377	Approved
0.5818	Remote Similarity	NPD6649	Approved
0.5818	Remote Similarity	NPD6869	Approved
0.5818	Remote Similarity	NPD8130	Phase 1
0.5818	Remote Similarity	NPD6650	Approved
0.5818	Remote Similarity	NPD6617	Approved
0.5818	Remote Similarity	NPD6847	Approved
0.5816	Remote Similarity	NPD6051	Approved
0.5816	Remote Similarity	NPD6101	Approved
0.5816	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5211	Phase 2
0.5806	Remote Similarity	NPD4790	Discontinued
0.5802	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6675	Approved
0.5794	Remote Similarity	NPD7128	Approved
0.5794	Remote Similarity	NPD5739	Approved
0.5794	Remote Similarity	NPD6402	Approved
0.5784	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6014	Approved
0.578	Remote Similarity	NPD6013	Approved
0.578	Remote Similarity	NPD6012	Approved
0.5776	Remote Similarity	NPD6016	Approved
0.5776	Remote Similarity	NPD8335	Approved
0.5776	Remote Similarity	NPD8378	Approved
0.5776	Remote Similarity	NPD8380	Approved
0.5776	Remote Similarity	NPD8296	Approved
0.5776	Remote Similarity	NPD8379	Approved
0.5776	Remote Similarity	NPD8033	Approved
0.5776	Remote Similarity	NPD6015	Approved
0.5769	Remote Similarity	NPD5286	Approved
0.5769	Remote Similarity	NPD5285	Approved
0.5769	Remote Similarity	NPD4696	Approved
0.5766	Remote Similarity	NPD8297	Approved
0.5763	Remote Similarity	NPD7492	Approved
0.5761	Remote Similarity	NPD4195	Approved
0.5755	Remote Similarity	NPD6647	Phase 2
0.5729	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5988	Approved
0.5714	Remote Similarity	NPD6616	Approved
0.5702	Remote Similarity	NPD7500	Approved
0.5701	Remote Similarity	NPD5141	Approved
0.57	Remote Similarity	NPD6411	Approved
0.57	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.57	Remote Similarity	NPD6079	Approved
0.5699	Remote Similarity	NPD7514	Phase 3
0.5699	Remote Similarity	NPD7332	Phase 2
0.569	Remote Similarity	NPD6059	Approved
0.5688	Remote Similarity	NPD7320	Approved
0.5688	Remote Similarity	NPD6011	Approved
0.5686	Remote Similarity	NPD5210	Approved
0.5686	Remote Similarity	NPD5695	Phase 3
0.5686	Remote Similarity	NPD4629	Approved
0.5684	Remote Similarity	NPD6110	Phase 1
0.5678	Remote Similarity	NPD7829	Approved
0.5678	Remote Similarity	NPD7830	Approved
0.5667	Remote Similarity	NPD8264	Approved
0.5667	Remote Similarity	NPD8074	Phase 3
0.5667	Remote Similarity	NPD7078	Approved
0.566	Remote Similarity	NPD5225	Approved
0.566	Remote Similarity	NPD5224	Approved
0.566	Remote Similarity	NPD5226	Approved
0.566	Remote Similarity	NPD4633	Approved
0.5657	Remote Similarity	NPD4753	Phase 2
0.5657	Remote Similarity	NPD1695	Approved
0.5657	Remote Similarity	NPD5370	Suspended
0.5652	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6399	Phase 3
0.5636	Remote Similarity	NPD6372	Approved
0.5636	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6373	Approved
0.5625	Remote Similarity	NPD3665	Phase 1
0.5625	Remote Similarity	NPD3133	Approved
0.5625	Remote Similarity	NPD3666	Approved
0.562	Remote Similarity	NPD7736	Approved
0.5612	Remote Similarity	NPD7750	Discontinued
0.5612	Remote Similarity	NPD7524	Approved
0.561	Remote Similarity	NPD1145	Discontinued
0.5607	Remote Similarity	NPD5174	Approved
0.5607	Remote Similarity	NPD5175	Approved
0.56	Remote Similarity	NPD8522	Clinical (unspecified phase)

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