NPASS Compound

Structure

CID122418 OpenBabel06191715472D 31 35 0 0 1 0 0 0 0 0999 V2000 -5.0518 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3679 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4981 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0120 -0.6164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2098 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -2.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3679 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2098 0.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3679 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6839 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -0.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5259 -2.4306 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5259 0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5259 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8420 -1.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8420 0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3679 -2.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 1 1 6 0 0 0 19 20 1 0 0 0 0 20 2 1 1 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 1 6 0 0 0 25 27 1 6 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.39
Volume:	490.807
LogP:	7.47
LogD:	5.971
LogS:	-6.867
# Rotatable Bonds:	0
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	4.695
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.17
MDCK Permeability:	1.0485308848728891e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.817
30% Bioavailability (F30%):	0.918

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	98.36271667480469%
Volume Distribution (VD):	1.309
Pgp-substrate:	1.4860585927963257%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.506
CYP2C19-inhibitor:	0.125
CYP2C19-substrate:	0.957
CYP2C9-inhibitor:	0.171
CYP2C9-substrate:	0.461
CYP2D6-inhibitor:	0.125
CYP2D6-substrate:	0.637
CYP3A4-inhibitor:	0.578
CYP3A4-substrate:	0.722

ADMET: Excretion

Clearance (CL):	4.409
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.286
Carcinogencity:	0.005
Eye Corrosion:	0.704
Eye Irritation:	0.86
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC122418

Natural Product ID:	NPC122418
*Common Name:**	3Alpha-Hydroxyurs-12-Ene
IUPAC Name:	(3R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-ol
Synonyms:
Standard InCHIKey:	FSLPMRQHCOLESF-ACUMZOKISA-N
Standard InCHI:	InChI=1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h9,19-20,22-25,31H,10-18H2,1-8H3/t19-,20+,22+,23-,24-,25+,27-,28+,29-,30-/m1/s1
SMILES:	C[C@@H]1CC[C@]2([C@@H]([C@H]1C)C1=CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@H](C1(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461182
PubChem CID:	12358389
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
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104489]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26020634]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8229021]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	128.0	ug.mL-1	PMID[566113]

☑ 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 NPC122418 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	212
0.1-0.2	1933
0.2-0.3	8365
0.3-0.4	16371
0.4-0.5	6344
0.5-0.6	4788
0.6-0.7	3337
0.7-0.8	969
0.8-0.85	237
0.85-0.9	101
0.9-0.95	13
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC290598
1.0	High Similarity	NPC30590
1.0	High Similarity	NPC265328
1.0	High Similarity	NPC27765
1.0	High Similarity	NPC120098
0.9859	High Similarity	NPC157996
0.9859	High Similarity	NPC40394
0.9859	High Similarity	NPC101475
0.9859	High Similarity	NPC34177
0.9857	High Similarity	NPC138374
0.9857	High Similarity	NPC34700
0.9722	High Similarity	NPC196753
0.9722	High Similarity	NPC99168
0.9722	High Similarity	NPC474989
0.9722	High Similarity	NPC158662
0.9722	High Similarity	NPC98386
0.9722	High Similarity	NPC253807
0.9722	High Similarity	NPC22955
0.9722	High Similarity	NPC470396
0.9722	High Similarity	NPC300499
0.9722	High Similarity	NPC230295
0.9718	High Similarity	NPC106364
0.9714	High Similarity	NPC100334
0.9589	High Similarity	NPC291379
0.9589	High Similarity	NPC53744
0.9459	High Similarity	NPC295131
0.9333	High Similarity	NPC242350
0.9315	High Similarity	NPC90979
0.9315	High Similarity	NPC472805
0.9296	High Similarity	NPC182717
0.9211	High Similarity	NPC47763
0.9211	High Similarity	NPC304285
0.9189	High Similarity	NPC72507
0.9155	High Similarity	NPC301226
0.9091	High Similarity	NPC253402
0.9091	High Similarity	NPC159168
0.9079	High Similarity	NPC116202
0.9028	High Similarity	NPC211009
0.8974	High Similarity	NPC238992
0.8919	High Similarity	NPC189883
0.8919	High Similarity	NPC237460
0.8904	High Similarity	NPC477138
0.8904	High Similarity	NPC243342
0.8904	High Similarity	NPC91858
0.8889	High Similarity	NPC110799
0.8889	High Similarity	NPC167706
0.8861	High Similarity	NPC191965
0.8861	High Similarity	NPC133954
0.8846	High Similarity	NPC82538
0.8846	High Similarity	NPC237795
0.88	High Similarity	NPC470758
0.88	High Similarity	NPC471798
0.88	High Similarity	NPC470711
0.8784	High Similarity	NPC141071
0.8784	High Similarity	NPC291503
0.8784	High Similarity	NPC66566
0.8784	High Similarity	NPC257347
0.8784	High Similarity	NPC471723
0.8784	High Similarity	NPC477923
0.8784	High Similarity	NPC144075
0.8767	High Similarity	NPC471799
0.875	High Similarity	NPC137306
0.875	High Similarity	NPC84121
0.875	High Similarity	NPC95594
0.875	High Similarity	NPC475862
0.875	High Similarity	NPC213412
0.875	High Similarity	NPC237344
0.875	High Similarity	NPC74363
0.875	High Similarity	NPC145498
0.875	High Similarity	NPC235341
0.875	High Similarity	NPC477579
0.8732	High Similarity	NPC94192
0.8732	High Similarity	NPC208999
0.8718	High Similarity	NPC248886
0.8684	High Similarity	NPC65897
0.8684	High Similarity	NPC138621
0.8684	High Similarity	NPC167037
0.8684	High Similarity	NPC312328
0.8684	High Similarity	NPC244385
0.8684	High Similarity	NPC285761
0.8684	High Similarity	NPC302041
0.8684	High Similarity	NPC6978
0.8684	High Similarity	NPC85346
0.8667	High Similarity	NPC106432
0.8667	High Similarity	NPC470749
0.8667	High Similarity	NPC240604
0.8667	High Similarity	NPC134330
0.8667	High Similarity	NPC202642
0.8667	High Similarity	NPC46160
0.8667	High Similarity	NPC129165
0.8667	High Similarity	NPC300324
0.8649	High Similarity	NPC192638
0.8649	High Similarity	NPC25511
0.8649	High Similarity	NPC62657
0.8649	High Similarity	NPC471797
0.8642	High Similarity	NPC51700
0.8642	High Similarity	NPC73064
0.8642	High Similarity	NPC293564
0.8642	High Similarity	NPC68160
0.8642	High Similarity	NPC307426
0.8642	High Similarity	NPC242468
0.8642	High Similarity	NPC130577
0.8642	High Similarity	NPC102683
0.8642	High Similarity	NPC18064
0.8642	High Similarity	NPC88716
0.8642	High Similarity	NPC98442
0.8642	High Similarity	NPC171203
0.8642	High Similarity	NPC142415
0.863	High Similarity	NPC242001
0.8592	High Similarity	NPC197805
0.8571	High Similarity	NPC472463
0.8571	High Similarity	NPC1319
0.8571	High Similarity	NPC80530
0.8571	High Similarity	NPC273410
0.8553	High Similarity	NPC91594
0.8553	High Similarity	NPC477924
0.8553	High Similarity	NPC214570
0.8553	High Similarity	NPC130136
0.8537	High Similarity	NPC52169
0.8537	High Similarity	NPC40552
0.8537	High Similarity	NPC181225
0.8537	High Similarity	NPC470629
0.8537	High Similarity	NPC290690
0.8537	High Similarity	NPC182797
0.8537	High Similarity	NPC17733
0.8537	High Similarity	NPC246708
0.8537	High Similarity	NPC473242
0.8537	High Similarity	NPC474512
0.8533	High Similarity	NPC118508
0.8533	High Similarity	NPC162742
0.8533	High Similarity	NPC230301
0.8533	High Similarity	NPC304309
0.8533	High Similarity	NPC288035
0.8533	High Similarity	NPC285893
0.8533	High Similarity	NPC212879
0.8533	High Similarity	NPC22105
0.8533	High Similarity	NPC240235
0.8533	High Similarity	NPC121744
0.8533	High Similarity	NPC104387
0.8533	High Similarity	NPC28657
0.8533	High Similarity	NPC134847
0.8533	High Similarity	NPC231256
0.8533	High Similarity	NPC178383
0.8533	High Similarity	NPC322353
0.8533	High Similarity	NPC136188
0.8519	High Similarity	NPC72638
0.85	High Similarity	NPC209802
0.85	High Similarity	NPC180834
0.8493	Intermediate Similarity	NPC92801
0.8493	Intermediate Similarity	NPC45296
0.8462	Intermediate Similarity	NPC102253
0.8462	Intermediate Similarity	NPC322313
0.8462	Intermediate Similarity	NPC236237
0.8462	Intermediate Similarity	NPC13554
0.8462	Intermediate Similarity	NPC236112
0.8451	Intermediate Similarity	NPC476039
0.8451	Intermediate Similarity	NPC222366
0.8451	Intermediate Similarity	NPC286669
0.8442	Intermediate Similarity	NPC275910
0.8442	Intermediate Similarity	NPC318136
0.8442	Intermediate Similarity	NPC205455
0.8442	Intermediate Similarity	NPC11908
0.8442	Intermediate Similarity	NPC186191
0.8434	Intermediate Similarity	NPC161751
0.8434	Intermediate Similarity	NPC130520
0.8434	Intermediate Similarity	NPC290972
0.8434	Intermediate Similarity	NPC274330
0.8434	Intermediate Similarity	NPC121798
0.8434	Intermediate Similarity	NPC263393
0.8434	Intermediate Similarity	NPC64872
0.8434	Intermediate Similarity	NPC95246
0.8434	Intermediate Similarity	NPC259875
0.8434	Intermediate Similarity	NPC127689
0.8434	Intermediate Similarity	NPC187785
0.8434	Intermediate Similarity	NPC470588
0.8434	Intermediate Similarity	NPC474972
0.8434	Intermediate Similarity	NPC61543
0.8434	Intermediate Similarity	NPC69627
0.8434	Intermediate Similarity	NPC59263
0.8434	Intermediate Similarity	NPC293048
0.8434	Intermediate Similarity	NPC225585
0.8434	Intermediate Similarity	NPC234346
0.8434	Intermediate Similarity	NPC270768
0.8434	Intermediate Similarity	NPC25906
0.8434	Intermediate Similarity	NPC198664
0.8434	Intermediate Similarity	NPC143232
0.8429	Intermediate Similarity	NPC225415
0.8421	Intermediate Similarity	NPC14112
0.8421	Intermediate Similarity	NPC321016
0.8421	Intermediate Similarity	NPC113733
0.8421	Intermediate Similarity	NPC470362
0.8421	Intermediate Similarity	NPC265588
0.8421	Intermediate Similarity	NPC321381
0.8421	Intermediate Similarity	NPC73875
0.8421	Intermediate Similarity	NPC278091
0.8421	Intermediate Similarity	NPC86305
0.8421	Intermediate Similarity	NPC477925
0.8421	Intermediate Similarity	NPC93662
0.8421	Intermediate Similarity	NPC107059
0.8421	Intermediate Similarity	NPC78067

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 NPC122418 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	2164
0.2-0.3	4232
0.3-0.4	1825
0.4-0.5	356
0.5-0.6	192
0.6-0.7	141
0.7-0.8	13
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9589	High Similarity	NPD7645	Phase 2
0.8533	High Similarity	NPD7339	Approved
0.8533	High Similarity	NPD6942	Approved
0.8462	Intermediate Similarity	NPD7525	Registered
0.8235	Intermediate Similarity	NPD7515	Phase 2
0.8182	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7748	Approved
0.7662	Intermediate Similarity	NPD4243	Approved
0.7647	Intermediate Similarity	NPD3618	Phase 1
0.7619	Intermediate Similarity	NPD4786	Approved
0.759	Intermediate Similarity	NPD3667	Approved
0.7586	Intermediate Similarity	NPD5328	Approved
0.7582	Intermediate Similarity	NPD7902	Approved
0.7529	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6924	Approved
0.7468	Intermediate Similarity	NPD4785	Approved
0.7468	Intermediate Similarity	NPD6926	Approved
0.7468	Intermediate Similarity	NPD4784	Approved
0.7436	Intermediate Similarity	NPD7151	Approved
0.7436	Intermediate Similarity	NPD7150	Approved
0.7436	Intermediate Similarity	NPD7152	Approved
0.7416	Intermediate Similarity	NPD6079	Approved
0.7403	Intermediate Similarity	NPD6923	Approved
0.7403	Intermediate Similarity	NPD6922	Approved
0.7375	Intermediate Similarity	NPD8264	Approved
0.7308	Intermediate Similarity	NPD7143	Approved
0.7308	Intermediate Similarity	NPD7144	Approved
0.7284	Intermediate Similarity	NPD6933	Approved
0.7253	Intermediate Similarity	NPD7900	Approved
0.7253	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3666	Approved
0.7209	Intermediate Similarity	NPD3665	Phase 1
0.7209	Intermediate Similarity	NPD3133	Approved
0.716	Intermediate Similarity	NPD5275	Approved
0.716	Intermediate Similarity	NPD4190	Phase 3
0.7159	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4202	Approved
0.7143	Intermediate Similarity	NPD4748	Discontinued
0.7143	Intermediate Similarity	NPD7509	Discontinued
0.7024	Intermediate Similarity	NPD6929	Approved
0.6947	Remote Similarity	NPD7638	Approved
0.6941	Remote Similarity	NPD6931	Approved
0.6941	Remote Similarity	NPD6930	Phase 2
0.6915	Remote Similarity	NPD5222	Approved
0.6915	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5221	Approved
0.6915	Remote Similarity	NPD4697	Phase 3
0.6875	Remote Similarity	NPD7639	Approved
0.6875	Remote Similarity	NPD7640	Approved
0.6848	Remote Similarity	NPD8035	Phase 2
0.6848	Remote Similarity	NPD8034	Phase 2
0.6842	Remote Similarity	NPD5173	Approved
0.6842	Remote Similarity	NPD4755	Approved
0.6824	Remote Similarity	NPD4195	Approved
0.6818	Remote Similarity	NPD3668	Phase 3
0.6786	Remote Similarity	NPD5776	Phase 2
0.6786	Remote Similarity	NPD6925	Approved
0.6786	Remote Similarity	NPD6932	Approved
0.6774	Remote Similarity	NPD6399	Phase 3
0.6771	Remote Similarity	NPD5290	Discontinued
0.675	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD368	Approved
0.6706	Remote Similarity	NPD7145	Approved
0.6706	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6695	Phase 3
0.6703	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4700	Approved
0.6701	Remote Similarity	NPD5285	Approved
0.6701	Remote Similarity	NPD5286	Approved
0.6701	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6633	Remote Similarity	NPD5223	Approved
0.663	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4753	Phase 2
0.6629	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6683	Phase 2
0.6591	Remote Similarity	NPD4221	Approved
0.6591	Remote Similarity	NPD4223	Phase 3
0.6575	Remote Similarity	NPD342	Phase 1
0.6566	Remote Similarity	NPD5211	Phase 2
0.6566	Remote Similarity	NPD5224	Approved
0.6566	Remote Similarity	NPD5225	Approved
0.6566	Remote Similarity	NPD4633	Approved
0.6566	Remote Similarity	NPD5226	Approved
0.6556	Remote Similarity	NPD6893	Approved
0.6556	Remote Similarity	NPD5329	Approved
0.6552	Remote Similarity	NPD7332	Phase 2
0.6552	Remote Similarity	NPD4695	Discontinued
0.6552	Remote Similarity	NPD7514	Phase 3
0.6535	Remote Similarity	NPD6402	Approved
0.6535	Remote Similarity	NPD5739	Approved
0.6535	Remote Similarity	NPD7128	Approved
0.6535	Remote Similarity	NPD6675	Approved
0.6517	Remote Similarity	NPD4788	Approved
0.65	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD4754	Approved
0.65	Remote Similarity	NPD5175	Approved
0.6484	Remote Similarity	NPD7521	Approved
0.6484	Remote Similarity	NPD6409	Approved
0.6484	Remote Similarity	NPD7334	Approved
0.6484	Remote Similarity	NPD5330	Approved
0.6484	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7146	Approved
0.6484	Remote Similarity	NPD6684	Approved
0.6477	Remote Similarity	NPD6902	Approved
0.6477	Remote Similarity	NPD6898	Phase 1
0.6463	Remote Similarity	NPD4787	Phase 1
0.6444	Remote Similarity	NPD4197	Approved
0.6436	Remote Similarity	NPD5141	Approved
0.6413	Remote Similarity	NPD3573	Approved
0.6413	Remote Similarity	NPD7750	Discontinued
0.6413	Remote Similarity	NPD7524	Approved
0.6408	Remote Similarity	NPD6899	Approved
0.6408	Remote Similarity	NPD7320	Approved
0.6408	Remote Similarity	NPD6881	Approved
0.6386	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4767	Approved
0.6373	Remote Similarity	NPD4768	Approved
0.6346	Remote Similarity	NPD6372	Approved
0.6346	Remote Similarity	NPD6373	Approved
0.6344	Remote Similarity	NPD6903	Approved
0.6341	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6084	Phase 2
0.6327	Remote Similarity	NPD6083	Phase 2
0.6322	Remote Similarity	NPD3617	Approved
0.6316	Remote Similarity	NPD6411	Approved
0.6311	Remote Similarity	NPD5697	Approved
0.6311	Remote Similarity	NPD5701	Approved
0.6304	Remote Similarity	NPD4688	Approved
0.6304	Remote Similarity	NPD4689	Approved
0.6304	Remote Similarity	NPD5205	Approved
0.6304	Remote Similarity	NPD4519	Discontinued
0.6304	Remote Similarity	NPD4690	Approved
0.6304	Remote Similarity	NPD4623	Approved
0.6304	Remote Similarity	NPD4693	Phase 3
0.6304	Remote Similarity	NPD4138	Approved
0.6289	Remote Similarity	NPD5210	Approved
0.6289	Remote Similarity	NPD4629	Approved
0.6286	Remote Similarity	NPD7290	Approved
0.6286	Remote Similarity	NPD6883	Approved
0.6286	Remote Similarity	NPD7102	Approved
0.6279	Remote Similarity	NPD6117	Approved
0.6277	Remote Similarity	NPD6051	Approved
0.6263	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD5168	Approved
0.625	Remote Similarity	NPD5128	Approved
0.625	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD4729	Approved
0.6238	Remote Similarity	NPD7632	Discontinued
0.6235	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6650	Approved
0.6226	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD8130	Phase 1
0.6226	Remote Similarity	NPD6617	Approved
0.6226	Remote Similarity	NPD6649	Approved
0.6226	Remote Similarity	NPD6869	Approved
0.6226	Remote Similarity	NPD6847	Approved
0.6224	Remote Similarity	NPD7614	Phase 1
0.6207	Remote Similarity	NPD6116	Phase 1
0.6195	Remote Similarity	NPD8328	Phase 3
0.619	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6012	Approved
0.619	Remote Similarity	NPD6014	Approved
0.619	Remote Similarity	NPD6013	Approved
0.618	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4723	Approved
0.617	Remote Similarity	NPD6672	Approved
0.617	Remote Similarity	NPD4722	Approved
0.617	Remote Similarity	NPD5737	Approved
0.6168	Remote Similarity	NPD8297	Approved
0.6168	Remote Similarity	NPD6882	Approved
0.6163	Remote Similarity	NPD3703	Phase 2
0.6154	Remote Similarity	NPD6412	Phase 2
0.6146	Remote Similarity	NPD7087	Discontinued
0.6143	Remote Similarity	NPD385	Approved
0.6143	Remote Similarity	NPD384	Approved
0.6139	Remote Similarity	NPD4159	Approved
0.6136	Remote Similarity	NPD6697	Approved
0.6136	Remote Similarity	NPD6118	Approved
0.6136	Remote Similarity	NPD6115	Approved
0.6136	Remote Similarity	NPD6114	Approved
0.6132	Remote Similarity	NPD5135	Approved
0.6132	Remote Similarity	NPD5169	Approved
0.6132	Remote Similarity	NPD5247	Approved
0.6132	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4634	Approved
0.6132	Remote Similarity	NPD5249	Phase 3
0.6132	Remote Similarity	NPD5248	Approved
0.6132	Remote Similarity	NPD5251	Approved
0.6132	Remote Similarity	NPD5250	Approved
0.6129	Remote Similarity	NPD4694	Approved
0.6129	Remote Similarity	NPD5690	Phase 2
0.6129	Remote Similarity	NPD5280	Approved
0.6105	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6101	Approved
0.6091	Remote Similarity	NPD7115	Discovery
0.6091	Remote Similarity	NPD8295	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