NPASS Compound

Structure

NPC169994 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 -2.0908 -0.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 1.1088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1248 -0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 7 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 6 0 0 0 14 17 1 0 0 0 0 14 20 1 6 0 0 0 15 20 1 6 0 0 0 15 22 1 0 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 18 4 1 6 0 0 0 18 23 1 0 0 0 0 19 5 1 6 0 0 0 19 23 1 0 0 0 0 20 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.25
Volume:	352.541
LogP:	3.588
LogD:	3.168
LogS:	-4.343
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.724
Synthetic Accessibility Score:	4.89
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.689
MDCK Permeability:	2.2288808395387605e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.403
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.606
Plasma Protein Binding (PPB):	84.46294403076172%
Volume Distribution (VD):	1.77
Pgp-substrate:	20.36823272705078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.765
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.9
CYP2C9-inhibitor:	0.102
CYP2C9-substrate:	0.242
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.45
CYP3A4-inhibitor:	0.742
CYP3A4-substrate:	0.419

ADMET: Excretion

Clearance (CL):	8.079
Half-life (T1/2):	0.367

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.542
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.844
Maximum Recommended Daily Dose:	0.279
Skin Sensitization:	0.219
Carcinogencity:	0.198
Eye Corrosion:	0.848
Eye Irritation:	0.162
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC169994

Natural Product ID:	NPC169994
*Common Name:**	1R,11S-Dihydroxy-8R,13R-Epoxylabd-14-Ene
IUPAC Name:	(1S,3R,4aR,6aS,10R,10aS,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromene-1,10-diol
Synonyms:
Standard InCHIKey:	PZRIIRZYKYWTJV-BGMRAPHESA-N
Standard InCHI:	InChI=1S/C20H34O3/c1-7-18(4)12-13(21)16-19(5,23-18)11-8-14-17(2,3)10-9-15(22)20(14,16)6/h7,13-16,21-22H,1,8-12H2,2-6H3/t13-,14-,15+,16-,18-,19+,20+/m0/s1
SMILES:	C=C[C@@]1(C)C[C@@H]([C@H]2[C@@](C)(CC[C@H]3C(C)(C)CC[C@H]([C@]23C)O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL559481
PubChem CID:	45267532
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
NPO25510	Plectranthus ernstii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19445517]
NPO25510	Plectranthus ernstii	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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1176	Organism	Mycobacterium fortuitum	Mycobacterium fortuitum	MIC	=	128.0	ug.mL-1	PMID[508789]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	128.0	ug.mL-1	PMID[508789]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	128.0	ug.mL-1	PMID[508789]

☑ 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 NPC169994 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	213
0.1-0.2	1987
0.2-0.3	6466
0.3-0.4	16076
0.4-0.5	7677
0.5-0.6	5828
0.6-0.7	3738
0.7-0.8	674
0.8-0.85	31
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9067	High Similarity	NPC137587
0.875	High Similarity	NPC210323
0.8611	High Similarity	NPC2648
0.8592	High Similarity	NPC42630
0.8519	High Similarity	NPC477578
0.8452	Intermediate Similarity	NPC261990
0.8452	Intermediate Similarity	NPC474249
0.8375	Intermediate Similarity	NPC155521
0.8356	Intermediate Similarity	NPC139785
0.8353	Intermediate Similarity	NPC289361
0.8312	Intermediate Similarity	NPC63958
0.8272	Intermediate Similarity	NPC470558
0.8243	Intermediate Similarity	NPC9942
0.8235	Intermediate Similarity	NPC92885
0.8235	Intermediate Similarity	NPC476226
0.8235	Intermediate Similarity	NPC77796
0.8171	Intermediate Similarity	NPC470077
0.8118	Intermediate Similarity	NPC59682
0.8077	Intermediate Similarity	NPC470766
0.8077	Intermediate Similarity	NPC106432
0.8072	Intermediate Similarity	NPC164424
0.8052	Intermediate Similarity	NPC91858
0.8049	Intermediate Similarity	NPC477978
0.8026	Intermediate Similarity	NPC167706
0.8025	Intermediate Similarity	NPC48673
0.8025	Intermediate Similarity	NPC20096
0.8	Intermediate Similarity	NPC476367
0.8	Intermediate Similarity	NPC72755
0.7975	Intermediate Similarity	NPC470758
0.7975	Intermediate Similarity	NPC470711
0.7975	Intermediate Similarity	NPC470750
0.7973	Intermediate Similarity	NPC117607
0.7973	Intermediate Similarity	NPC101307
0.7973	Intermediate Similarity	NPC185874
0.7973	Intermediate Similarity	NPC139207
0.7973	Intermediate Similarity	NPC88454
0.7949	Intermediate Similarity	NPC3403
0.7949	Intermediate Similarity	NPC291503
0.7927	Intermediate Similarity	NPC304285
0.7927	Intermediate Similarity	NPC470049
0.7922	Intermediate Similarity	NPC182717
0.7882	Intermediate Similarity	NPC149224
0.7882	Intermediate Similarity	NPC304083
0.7875	Intermediate Similarity	NPC301707
0.7875	Intermediate Similarity	NPC11908
0.7875	Intermediate Similarity	NPC148977
0.7875	Intermediate Similarity	NPC472501
0.7867	Intermediate Similarity	NPC276616
0.7865	Intermediate Similarity	NPC8774
0.7857	Intermediate Similarity	NPC274448
0.7857	Intermediate Similarity	NPC157257
0.7848	Intermediate Similarity	NPC470749
0.7848	Intermediate Similarity	NPC198473
0.7848	Intermediate Similarity	NPC265588
0.7841	Intermediate Similarity	NPC27531
0.7838	Intermediate Similarity	NPC476406
0.7831	Intermediate Similarity	NPC474789
0.7831	Intermediate Similarity	NPC52108
0.7821	Intermediate Similarity	NPC476366
0.7821	Intermediate Similarity	NPC477138
0.7821	Intermediate Similarity	NPC243342
0.7821	Intermediate Similarity	NPC71152
0.7821	Intermediate Similarity	NPC201048
0.7821	Intermediate Similarity	NPC471797
0.7808	Intermediate Similarity	NPC101128
0.7805	Intermediate Similarity	NPC249423
0.7805	Intermediate Similarity	NPC476646
0.7792	Intermediate Similarity	NPC110799
0.7791	Intermediate Similarity	NPC212596
0.7791	Intermediate Similarity	NPC475605
0.7791	Intermediate Similarity	NPC4574
0.7791	Intermediate Similarity	NPC471952
0.7778	Intermediate Similarity	NPC273410
0.7778	Intermediate Similarity	NPC80530
0.7778	Intermediate Similarity	NPC12103
0.7778	Intermediate Similarity	NPC227583
0.7778	Intermediate Similarity	NPC98457
0.7765	Intermediate Similarity	NPC299068
0.7753	Intermediate Similarity	NPC65402
0.7753	Intermediate Similarity	NPC127718
0.7753	Intermediate Similarity	NPC144202
0.775	Intermediate Similarity	NPC307336
0.775	Intermediate Similarity	NPC138502
0.775	Intermediate Similarity	NPC470751
0.775	Intermediate Similarity	NPC91594
0.775	Intermediate Similarity	NPC471798
0.775	Intermediate Similarity	NPC472746
0.775	Intermediate Similarity	NPC260301
0.7738	Intermediate Similarity	NPC86238
0.7738	Intermediate Similarity	NPC15534
0.7733	Intermediate Similarity	NPC253303
0.7733	Intermediate Similarity	NPC269077
0.7722	Intermediate Similarity	NPC144075
0.7722	Intermediate Similarity	NPC185536
0.7722	Intermediate Similarity	NPC103822
0.7711	Intermediate Similarity	NPC471408
0.7711	Intermediate Similarity	NPC218616
0.7711	Intermediate Similarity	NPC296701
0.7703	Intermediate Similarity	NPC60837
0.7703	Intermediate Similarity	NPC2728
0.7703	Intermediate Similarity	NPC172613
0.7703	Intermediate Similarity	NPC258595
0.7703	Intermediate Similarity	NPC64123
0.7703	Intermediate Similarity	NPC282619
0.7703	Intermediate Similarity	NPC11555
0.7703	Intermediate Similarity	NPC208198
0.7701	Intermediate Similarity	NPC101886
0.7701	Intermediate Similarity	NPC138974
0.7692	Intermediate Similarity	NPC68443
0.7692	Intermediate Similarity	NPC471799
0.7692	Intermediate Similarity	NPC211009
0.7683	Intermediate Similarity	NPC96362
0.7683	Intermediate Similarity	NPC236237
0.7683	Intermediate Similarity	NPC322313
0.7683	Intermediate Similarity	NPC102253
0.7674	Intermediate Similarity	NPC166857
0.7674	Intermediate Similarity	NPC476948
0.7662	Intermediate Similarity	NPC283316
0.7662	Intermediate Similarity	NPC282454
0.7662	Intermediate Similarity	NPC45296
0.7654	Intermediate Similarity	NPC244385
0.7654	Intermediate Similarity	NPC167037
0.7654	Intermediate Similarity	NPC31828
0.7654	Intermediate Similarity	NPC300499
0.7654	Intermediate Similarity	NPC6978
0.7654	Intermediate Similarity	NPC98386
0.7654	Intermediate Similarity	NPC253807
0.7654	Intermediate Similarity	NPC285761
0.7654	Intermediate Similarity	NPC158662
0.7654	Intermediate Similarity	NPC196753
0.7654	Intermediate Similarity	NPC472342
0.7654	Intermediate Similarity	NPC138621
0.7654	Intermediate Similarity	NPC230295
0.7647	Intermediate Similarity	NPC266511
0.7647	Intermediate Similarity	NPC470360
0.7632	Intermediate Similarity	NPC244790
0.7632	Intermediate Similarity	NPC245795
0.7625	Intermediate Similarity	NPC91573
0.7625	Intermediate Similarity	NPC38141
0.7625	Intermediate Similarity	NPC14112
0.7625	Intermediate Similarity	NPC278091
0.7625	Intermediate Similarity	NPC86305
0.7625	Intermediate Similarity	NPC78067
0.7625	Intermediate Similarity	NPC93662
0.7619	Intermediate Similarity	NPC134481
0.7619	Intermediate Similarity	NPC470929
0.7619	Intermediate Similarity	NPC82623
0.7614	Intermediate Similarity	NPC295668
0.7595	Intermediate Similarity	NPC100334
0.7595	Intermediate Similarity	NPC472503
0.7595	Intermediate Similarity	NPC308440
0.7595	Intermediate Similarity	NPC476736
0.759	Intermediate Similarity	NPC7505
0.759	Intermediate Similarity	NPC142163
0.759	Intermediate Similarity	NPC474731
0.759	Intermediate Similarity	NPC474759
0.759	Intermediate Similarity	NPC157655
0.759	Intermediate Similarity	NPC70927
0.759	Intermediate Similarity	NPC116202
0.759	Intermediate Similarity	NPC474752
0.759	Intermediate Similarity	NPC474683
0.759	Intermediate Similarity	NPC82986
0.7582	Intermediate Similarity	NPC288970
0.7568	Intermediate Similarity	NPC68656
0.7568	Intermediate Similarity	NPC144650
0.7564	Intermediate Similarity	NPC242001
0.7564	Intermediate Similarity	NPC157422
0.7564	Intermediate Similarity	NPC471272
0.7564	Intermediate Similarity	NPC100586
0.7564	Intermediate Similarity	NPC301226
0.7564	Intermediate Similarity	NPC109457
0.7564	Intermediate Similarity	NPC111234
0.7564	Intermediate Similarity	NPC164022
0.7561	Intermediate Similarity	NPC291379
0.7561	Intermediate Similarity	NPC233295
0.7561	Intermediate Similarity	NPC24504
0.7561	Intermediate Similarity	NPC476316
0.7561	Intermediate Similarity	NPC53744
0.7561	Intermediate Similarity	NPC5604
0.7558	Intermediate Similarity	NPC6605
0.7558	Intermediate Similarity	NPC125399
0.7556	Intermediate Similarity	NPC201725
0.7532	Intermediate Similarity	NPC234511
0.7531	Intermediate Similarity	NPC34177
0.7531	Intermediate Similarity	NPC157996
0.7531	Intermediate Similarity	NPC477924
0.7531	Intermediate Similarity	NPC130136
0.7531	Intermediate Similarity	NPC90979
0.7531	Intermediate Similarity	NPC40394
0.7531	Intermediate Similarity	NPC212241
0.7531	Intermediate Similarity	NPC248830
0.7531	Intermediate Similarity	NPC331618
0.7531	Intermediate Similarity	NPC119355
0.7531	Intermediate Similarity	NPC472805
0.7531	Intermediate Similarity	NPC257191
0.7531	Intermediate Similarity	NPC101475
0.7529	Intermediate Similarity	NPC474047
0.7529	Intermediate Similarity	NPC205845
0.7529	Intermediate Similarity	NPC46320
0.7528	Intermediate Similarity	NPC130840

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 NPC169994 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	2345
0.2-0.3	3999
0.3-0.4	1865
0.4-0.5	413
0.5-0.6	192
0.6-0.7	140
0.7-0.8	5
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
0.7778	Intermediate Similarity	NPD7645	Phase 2
0.7683	Intermediate Similarity	NPD7525	Registered
0.7172	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7339	Approved
0.7073	Intermediate Similarity	NPD6942	Approved
0.6988	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7638	Approved
0.6818	Remote Similarity	NPD6695	Phase 3
0.6804	Remote Similarity	NPD7639	Approved
0.6804	Remote Similarity	NPD7640	Approved
0.6747	Remote Similarity	NPD6926	Approved
0.6747	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD371	Approved
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD7509	Discontinued
0.6596	Remote Similarity	NPD6079	Approved
0.6596	Remote Similarity	NPD8035	Phase 2
0.6596	Remote Similarity	NPD8034	Phase 2
0.6593	Remote Similarity	NPD3618	Phase 1
0.6588	Remote Similarity	NPD6933	Approved
0.6585	Remote Similarity	NPD4787	Phase 1
0.6566	Remote Similarity	NPD4159	Approved
0.6559	Remote Similarity	NPD5328	Approved
0.6556	Remote Similarity	NPD4786	Approved
0.6552	Remote Similarity	NPD6929	Approved
0.6548	Remote Similarity	NPD4784	Approved
0.6548	Remote Similarity	NPD4785	Approved
0.6531	Remote Similarity	NPD4225	Approved
0.6526	Remote Similarity	NPD4202	Approved
0.6522	Remote Similarity	NPD7524	Approved
0.6522	Remote Similarity	NPD7750	Discontinued
0.6522	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3667	Approved
0.6512	Remote Similarity	NPD6932	Approved
0.6506	Remote Similarity	NPD4243	Approved
0.6506	Remote Similarity	NPD7151	Approved
0.6506	Remote Similarity	NPD7152	Approved
0.6506	Remote Similarity	NPD7150	Approved
0.6505	Remote Similarity	NPD6881	Approved
0.6505	Remote Similarity	NPD6899	Approved
0.65	Remote Similarity	NPD5211	Phase 2
0.6477	Remote Similarity	NPD7514	Phase 3
0.6477	Remote Similarity	NPD4748	Discontinued
0.6477	Remote Similarity	NPD6928	Phase 2
0.6477	Remote Similarity	NPD7332	Phase 2
0.6471	Remote Similarity	NPD5739	Approved
0.6471	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD6675	Approved
0.6471	Remote Similarity	NPD6402	Approved
0.6465	Remote Similarity	NPD5285	Approved
0.6465	Remote Similarity	NPD4696	Approved
0.6465	Remote Similarity	NPD5286	Approved
0.6458	Remote Similarity	NPD7748	Approved
0.6437	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7145	Approved
0.6429	Remote Similarity	NPD4755	Approved
0.6429	Remote Similarity	NPD7902	Approved
0.6422	Remote Similarity	NPD7328	Approved
0.6422	Remote Similarity	NPD7327	Approved
0.6421	Remote Similarity	NPD7515	Phase 2
0.6408	Remote Similarity	NPD5697	Approved
0.6396	Remote Similarity	NPD6921	Approved
0.6386	Remote Similarity	NPD7144	Approved
0.6386	Remote Similarity	NPD7143	Approved
0.6383	Remote Similarity	NPD6051	Approved
0.6381	Remote Similarity	NPD7102	Approved
0.6381	Remote Similarity	NPD6883	Approved
0.6381	Remote Similarity	NPD7290	Approved
0.6373	Remote Similarity	NPD5141	Approved
0.6364	Remote Similarity	NPD7516	Approved
0.6355	Remote Similarity	NPD8133	Approved
0.6354	Remote Similarity	NPD6399	Phase 3
0.6346	Remote Similarity	NPD7320	Approved
0.6337	Remote Similarity	NPD7632	Discontinued
0.6337	Remote Similarity	NPD5224	Approved
0.6337	Remote Similarity	NPD4633	Approved
0.6337	Remote Similarity	NPD5226	Approved
0.6337	Remote Similarity	NPD5225	Approved
0.633	Remote Similarity	NPD7115	Discovery
0.6322	Remote Similarity	NPD6925	Approved
0.6322	Remote Similarity	NPD6116	Phase 1
0.6322	Remote Similarity	NPD5776	Phase 2
0.6321	Remote Similarity	NPD6869	Approved
0.6321	Remote Similarity	NPD6649	Approved
0.6321	Remote Similarity	NPD8130	Phase 1
0.6321	Remote Similarity	NPD6650	Approved
0.6321	Remote Similarity	NPD6617	Approved
0.6321	Remote Similarity	NPD6847	Approved
0.631	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD8294	Approved
0.6306	Remote Similarity	NPD8377	Approved
0.6304	Remote Similarity	NPD6893	Approved
0.63	Remote Similarity	NPD4700	Approved
0.6286	Remote Similarity	NPD6014	Approved
0.6286	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6372	Approved
0.6286	Remote Similarity	NPD6013	Approved
0.6286	Remote Similarity	NPD6012	Approved
0.6286	Remote Similarity	NPD6373	Approved
0.6275	Remote Similarity	NPD5174	Approved
0.6275	Remote Similarity	NPD5175	Approved
0.6265	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD6922	Approved
0.6265	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD6923	Approved
0.6264	Remote Similarity	NPD4788	Approved
0.6262	Remote Similarity	NPD8297	Approved
0.6262	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD8335	Approved
0.625	Remote Similarity	NPD7503	Approved
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD8033	Approved
0.625	Remote Similarity	NPD8296	Approved
0.625	Remote Similarity	NPD8380	Approved
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD7087	Discontinued
0.625	Remote Similarity	NPD8378	Approved
0.625	Remote Similarity	NPD8379	Approved
0.6238	Remote Similarity	NPD5344	Discontinued
0.6238	Remote Similarity	NPD5223	Approved
0.6222	Remote Similarity	NPD6902	Approved
0.6222	Remote Similarity	NPD6898	Phase 1
0.6207	Remote Similarity	NPD6117	Approved
0.6203	Remote Similarity	NPD368	Approved
0.6196	Remote Similarity	NPD3665	Phase 1
0.6196	Remote Similarity	NPD3666	Approved
0.6196	Remote Similarity	NPD3133	Approved
0.619	Remote Similarity	NPD6011	Approved
0.619	Remote Similarity	NPD6686	Approved
0.618	Remote Similarity	NPD4195	Approved
0.618	Remote Similarity	NPD6683	Phase 2
0.617	Remote Similarity	NPD3573	Approved
0.6163	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5221	Approved
0.6162	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5222	Approved
0.6122	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7900	Approved
0.61	Remote Similarity	NPD6083	Phase 2
0.61	Remote Similarity	NPD5173	Approved
0.61	Remote Similarity	NPD6084	Phase 2
0.6092	Remote Similarity	NPD5275	Approved
0.6092	Remote Similarity	NPD4190	Phase 3
0.6092	Remote Similarity	NPD3703	Phase 2
0.6075	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6118	Approved
0.6067	Remote Similarity	NPD6114	Approved
0.6067	Remote Similarity	NPD6115	Approved
0.6067	Remote Similarity	NPD6697	Approved
0.6056	Remote Similarity	NPD384	Approved
0.6056	Remote Similarity	NPD385	Approved
0.6042	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4753	Phase 2
0.6042	Remote Similarity	NPD6101	Approved
0.604	Remote Similarity	NPD5290	Discontinued
0.6038	Remote Similarity	NPD4729	Approved
0.6038	Remote Similarity	NPD4730	Approved
0.6034	Remote Similarity	NPD7507	Approved
0.6019	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD4244	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD4245	Approved
0.5981	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6648	Approved
0.5977	Remote Similarity	NPD1811	Approved
0.5977	Remote Similarity	NPD1810	Approved
0.5962	Remote Similarity	NPD4754	Approved
0.5957	Remote Similarity	NPD1694	Approved
0.5952	Remote Similarity	NPD5360	Phase 3
0.5952	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6412	Phase 2
0.5929	Remote Similarity	NPD7100	Approved
0.5929	Remote Similarity	NPD7101	Approved
0.5926	Remote Similarity	NPD5248	Approved
0.5926	Remote Similarity	NPD5247	Approved
0.5926	Remote Similarity	NPD5249	Phase 3
0.5926	Remote Similarity	NPD4634	Approved
0.5926	Remote Similarity	NPD5250	Approved
0.5926	Remote Similarity	NPD5251	Approved
0.5918	Remote Similarity	NPD7637	Suspended
0.5909	Remote Similarity	NPD3702	Approved
0.59	Remote Similarity	NPD5210	Approved
0.59	Remote Similarity	NPD4629	Approved
0.5895	Remote Similarity	NPD6684	Approved
0.5895	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4623	Approved
0.5895	Remote Similarity	NPD4519	Discontinued
0.5895	Remote Similarity	NPD7334	Approved
0.5895	Remote Similarity	NPD5330	Approved
0.5895	Remote Similarity	NPD6409	Approved
0.5895	Remote Similarity	NPD7146	Approved
0.5895	Remote Similarity	NPD7521	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