NPASS Compound

Structure

CID66566 OpenBabel06191715402D 23 25 0 0 1 0 0 0 0 0999 V2000 0.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9239 -0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 3.0000 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 2.5981 0.5000 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 1.7321 3.0000 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 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 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 4.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 2 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 2 0 0 0 0 0 0 0 0 0 3.9641 3.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 2 0 0 0 0 0 0 0 0 0 5.4641 4.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 14 20 1 6 0 0 0 15 18 1 0 0 0 0 15 20 1 6 0 0 0 16 18 1 0 0 0 0 16 22 1 6 0 0 0 17 19 1 0 0 0 0 17 23 1 1 0 0 0 19 3 1 1 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.25
Volume:	352.541
LogP:	3.112
LogD:	2.693
LogS:	-2.511
# Rotatable Bonds:	2
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.684
Synthetic Accessibility Score:	4.616
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:	-4.744
MDCK Permeability:	8.702993000042625e-06
Pgp-inhibitor:	0.969
Pgp-substrate:	0.633
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.845
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.289
Plasma Protein Binding (PPB):	71.76342010498047%
Volume Distribution (VD):	0.891
Pgp-substrate:	20.67316436767578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.758
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.445
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	8.448
Half-life (T1/2):	0.261

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.342
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.237
Carcinogencity:	0.486
Eye Corrosion:	0.008
Eye Irritation:	0.128
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC66566

Natural Product ID:	NPC66566
*Common Name:**	Darutigenol
IUPAC Name:	(1R)-1-[(2S,4aR,4bS,7R,8aS)-7-hydroxy-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]ethane-1,2-diol
Synonyms:	Darutigenol
Standard InCHIKey:	NCAZLDCEJHFJDT-KHKZNYETSA-N
Standard InCHI:	InChI=1S/C20H34O3/c1-18(2)15-6-5-13-11-19(3,17(23)12-21)9-7-14(13)20(15,4)10-8-16(18)22/h11,14-17,21-23H,5-10,12H2,1-4H3/t14-,15-,16-,17+,19+,20+/m1/s1
SMILES:	OC[C@@H]([C@@]1(C)CC[C@@H]2C(=C1)CC[C@H]1[C@@]2(C)CC[C@H](C1(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076911
PubChem CID:	3037565
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO12604	Phakellia dendyi	Species	Bubaridae	Eukaryota	n.a.	Byron Strait, Papua New Guinea	2003	PMID[18327911]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19928884]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial part	n.a.	n.a.	PMID[24997688]
NPO26395	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28009521]
NPO30887	Siegesbeckia orientalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19831.1	Siegesbeckia orientalis var. glabrescens	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23241	Sigesbeckia orientalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30887	Siegesbeckia orientalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28940	Sigesbeckia glabrescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26395	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6819	Cardopatium corymbosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3034	Lonchocarpus yucatanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23241	Sigesbeckia orientalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7081	Sidastrum tehuacanum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3220	Aberia caffra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12604	Phakellia dendyi	Species	Bubaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1540	Scopolia tangutica	Species	Solanaceae	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	4
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[522349]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[522350]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[522350]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	25000.0	nM	PMID[522351]
NPT2533	Individual Protein	Coagulation factor X	Homo sapiens	IC50	=	11418.0	nM	PMID[522352]

☑ 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 NPC66566 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	182
0.1-0.2	1415
0.2-0.3	5660
0.3-0.4	15757
0.4-0.5	8887
0.5-0.6	5584
0.6-0.7	3724
0.7-0.8	1162
0.8-0.85	229
0.85-0.9	62
0.9-0.95	22
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477923
0.9718	High Similarity	NPC477924
0.9577	High Similarity	NPC274079
0.9577	High Similarity	NPC477925
0.9571	High Similarity	NPC243342
0.9571	High Similarity	NPC477138
0.9437	High Similarity	NPC291503
0.9324	High Similarity	NPC287749
0.9296	High Similarity	NPC91858
0.9286	High Similarity	NPC242001
0.92	High Similarity	NPC474531
0.9178	High Similarity	NPC130136
0.9178	High Similarity	NPC471798
0.9155	High Similarity	NPC471799
0.9155	High Similarity	NPC182717
0.9143	High Similarity	NPC145498
0.9067	High Similarity	NPC236112
0.9054	High Similarity	NPC167891
0.9054	High Similarity	NPC22955
0.9054	High Similarity	NPC470396
0.9054	High Similarity	NPC83351
0.9054	High Similarity	NPC99168
0.9054	High Similarity	NPC474989
0.9028	High Similarity	NPC471797
0.9028	High Similarity	NPC100334
0.9014	High Similarity	NPC167706
0.8933	High Similarity	NPC328714
0.8933	High Similarity	NPC291379
0.8933	High Similarity	NPC53744
0.8919	High Similarity	NPC472805
0.8919	High Similarity	NPC101475
0.8919	High Similarity	NPC40394
0.8919	High Similarity	NPC34177
0.8919	High Similarity	NPC91594
0.8919	High Similarity	NPC90979
0.8919	High Similarity	NPC157996
0.8873	High Similarity	NPC92801
0.8857	High Similarity	NPC208999
0.8846	High Similarity	NPC238992
0.8831	High Similarity	NPC47763
0.8831	High Similarity	NPC30166
0.8816	High Similarity	NPC96362
0.8816	High Similarity	NPC13554
0.88	High Similarity	NPC476314
0.88	High Similarity	NPC98386
0.88	High Similarity	NPC275910
0.88	High Similarity	NPC196753
0.88	High Similarity	NPC158662
0.88	High Similarity	NPC230295
0.88	High Similarity	NPC300499
0.88	High Similarity	NPC253807
0.8784	High Similarity	NPC30590
0.8784	High Similarity	NPC321016
0.8784	High Similarity	NPC265328
0.8784	High Similarity	NPC107059
0.8784	High Similarity	NPC120098
0.8784	High Similarity	NPC265588
0.8784	High Similarity	NPC290598
0.8784	High Similarity	NPC27765
0.8784	High Similarity	NPC300324
0.8784	High Similarity	NPC122418
0.8784	High Similarity	NPC189883
0.8784	High Similarity	NPC321381
0.8784	High Similarity	NPC240604
0.8784	High Similarity	NPC106432
0.8784	High Similarity	NPC106364
0.875	High Similarity	NPC110799
0.875	High Similarity	NPC242992
0.8718	High Similarity	NPC253402
0.8718	High Similarity	NPC317458
0.8718	High Similarity	NPC159168
0.8701	High Similarity	NPC476646
0.8701	High Similarity	NPC142163
0.8684	High Similarity	NPC472463
0.8684	High Similarity	NPC1319
0.8667	High Similarity	NPC470711
0.8667	High Similarity	NPC470758
0.8667	High Similarity	NPC214570
0.8667	High Similarity	NPC155986
0.8667	High Similarity	NPC198968
0.8667	High Similarity	NPC318495
0.8649	High Similarity	NPC304309
0.8649	High Similarity	NPC138374
0.8649	High Similarity	NPC141071
0.8649	High Similarity	NPC288035
0.8649	High Similarity	NPC285893
0.8649	High Similarity	NPC134847
0.8649	High Similarity	NPC34700
0.8649	High Similarity	NPC22105
0.8649	High Similarity	NPC136188
0.8649	High Similarity	NPC471723
0.8649	High Similarity	NPC162742
0.8649	High Similarity	NPC257347
0.8649	High Similarity	NPC230301
0.8649	High Similarity	NPC28657
0.863	High Similarity	NPC68443
0.8625	High Similarity	NPC237344
0.8625	High Similarity	NPC94462
0.8608	High Similarity	NPC185568
0.859	High Similarity	NPC248886
0.8571	High Similarity	NPC295131
0.8553	High Similarity	NPC473943
0.8553	High Similarity	NPC477522
0.8553	High Similarity	NPC244385
0.8553	High Similarity	NPC6978
0.8553	High Similarity	NPC285761
0.8553	High Similarity	NPC474216
0.8553	High Similarity	NPC138621
0.8553	High Similarity	NPC167037
0.8553	High Similarity	NPC87604
0.8553	High Similarity	NPC72507
0.8551	High Similarity	NPC225415
0.8551	High Similarity	NPC144650
0.8551	High Similarity	NPC290367
0.8533	High Similarity	NPC96319
0.8533	High Similarity	NPC237460
0.8533	High Similarity	NPC134330
0.8533	High Similarity	NPC202642
0.8533	High Similarity	NPC129165
0.8533	High Similarity	NPC470749
0.8533	High Similarity	NPC73875
0.8533	High Similarity	NPC113733
0.8533	High Similarity	NPC253190
0.8533	High Similarity	NPC46160
0.8514	High Similarity	NPC469534
0.8514	High Similarity	NPC469593
0.8514	High Similarity	NPC476366
0.8514	High Similarity	NPC201048
0.8514	High Similarity	NPC306727
0.8514	High Similarity	NPC469533
0.8493	Intermediate Similarity	NPC164022
0.8481	Intermediate Similarity	NPC474634
0.8481	Intermediate Similarity	NPC82538
0.8481	Intermediate Similarity	NPC207013
0.8481	Intermediate Similarity	NPC237795
0.8462	Intermediate Similarity	NPC470383
0.8462	Intermediate Similarity	NPC6707
0.8462	Intermediate Similarity	NPC249423
0.8462	Intermediate Similarity	NPC242350
0.8462	Intermediate Similarity	NPC116202
0.8451	Intermediate Similarity	NPC197805
0.8442	Intermediate Similarity	NPC109546
0.8442	Intermediate Similarity	NPC84694
0.8442	Intermediate Similarity	NPC30986
0.8442	Intermediate Similarity	NPC209430
0.8442	Intermediate Similarity	NPC80530
0.8442	Intermediate Similarity	NPC81306
0.8442	Intermediate Similarity	NPC100906
0.8442	Intermediate Similarity	NPC143182
0.8442	Intermediate Similarity	NPC28862
0.8442	Intermediate Similarity	NPC47982
0.8442	Intermediate Similarity	NPC273410
0.8421	Intermediate Similarity	NPC34019
0.84	Intermediate Similarity	NPC322353
0.84	Intermediate Similarity	NPC121744
0.84	Intermediate Similarity	NPC118508
0.8395	Intermediate Similarity	NPC477604
0.8395	Intermediate Similarity	NPC125399
0.8375	Intermediate Similarity	NPC319238
0.8375	Intermediate Similarity	NPC124172
0.8375	Intermediate Similarity	NPC209802
0.8356	Intermediate Similarity	NPC34834
0.8354	Intermediate Similarity	NPC470049
0.8354	Intermediate Similarity	NPC49964
0.8354	Intermediate Similarity	NPC304285
0.8354	Intermediate Similarity	NPC101462
0.8354	Intermediate Similarity	NPC201852
0.8354	Intermediate Similarity	NPC212083
0.8354	Intermediate Similarity	NPC48362
0.8333	Intermediate Similarity	NPC322313
0.8333	Intermediate Similarity	NPC22403
0.8333	Intermediate Similarity	NPC241290
0.8333	Intermediate Similarity	NPC236237
0.8333	Intermediate Similarity	NPC102253
0.8333	Intermediate Similarity	NPC94192
0.8333	Intermediate Similarity	NPC234193
0.8333	Intermediate Similarity	NPC164840
0.8333	Intermediate Similarity	NPC209944
0.8333	Intermediate Similarity	NPC26117
0.8333	Intermediate Similarity	NPC244790
0.8313	Intermediate Similarity	NPC105495
0.8313	Intermediate Similarity	NPC470361
0.8312	Intermediate Similarity	NPC85346
0.8312	Intermediate Similarity	NPC11908
0.8312	Intermediate Similarity	NPC148977
0.8312	Intermediate Similarity	NPC186191
0.8312	Intermediate Similarity	NPC302041
0.8312	Intermediate Similarity	NPC76931
0.8312	Intermediate Similarity	NPC65897
0.8312	Intermediate Similarity	NPC318136
0.8312	Intermediate Similarity	NPC307965
0.8312	Intermediate Similarity	NPC312328
0.8312	Intermediate Similarity	NPC18603
0.8312	Intermediate Similarity	NPC205455
0.831	Intermediate Similarity	NPC476039
0.831	Intermediate Similarity	NPC286669
0.831	Intermediate Similarity	NPC222366
0.8293	Intermediate Similarity	NPC477926
0.8293	Intermediate Similarity	NPC470620
0.8293	Intermediate Similarity	NPC189777

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 NPC66566 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1747
0.2-0.3	4120
0.3-0.4	2171
0.4-0.5	558
0.5-0.6	200
0.6-0.7	147
0.7-0.8	39
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD7645	Phase 2
0.8649	High Similarity	NPD6942	Approved
0.8649	High Similarity	NPD7339	Approved
0.8533	High Similarity	NPD3701	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7525	Registered
0.8289	Intermediate Similarity	NPD6933	Approved
0.8026	Intermediate Similarity	NPD6924	Approved
0.8026	Intermediate Similarity	NPD6926	Approved
0.7927	Intermediate Similarity	NPD4786	Approved
0.7922	Intermediate Similarity	NPD8264	Approved
0.7901	Intermediate Similarity	NPD3667	Approved
0.7763	Intermediate Similarity	NPD7151	Approved
0.7763	Intermediate Similarity	NPD7150	Approved
0.7763	Intermediate Similarity	NPD7152	Approved
0.7738	Intermediate Similarity	NPD3618	Phase 1
0.7733	Intermediate Similarity	NPD6923	Approved
0.7733	Intermediate Similarity	NPD6922	Approved
0.7674	Intermediate Similarity	NPD5328	Approved
0.7654	Intermediate Similarity	NPD7509	Discontinued
0.7632	Intermediate Similarity	NPD7143	Approved
0.7632	Intermediate Similarity	NPD7144	Approved
0.7564	Intermediate Similarity	NPD4785	Approved
0.7564	Intermediate Similarity	NPD4784	Approved
0.7532	Intermediate Similarity	NPD4243	Approved
0.7531	Intermediate Similarity	NPD6929	Approved
0.75	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD7515	Phase 2
0.7442	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4748	Discontinued
0.7439	Intermediate Similarity	NPD6930	Phase 2
0.7439	Intermediate Similarity	NPD6931	Approved
0.7294	Intermediate Similarity	NPD3666	Approved
0.7294	Intermediate Similarity	NPD3133	Approved
0.7294	Intermediate Similarity	NPD3665	Phase 1
0.7284	Intermediate Similarity	NPD6932	Approved
0.7284	Intermediate Similarity	NPD5776	Phase 2
0.7284	Intermediate Similarity	NPD6925	Approved
0.7241	Intermediate Similarity	NPD7524	Approved
0.7222	Intermediate Similarity	NPD4202	Approved
0.7195	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7145	Approved
0.7176	Intermediate Similarity	NPD6695	Phase 3
0.7143	Intermediate Similarity	NPD7748	Approved
0.7108	Intermediate Similarity	NPD6683	Phase 2
0.7093	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3668	Phase 3
0.7051	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4190	Phase 3
0.7037	Intermediate Similarity	NPD5275	Approved
0.7033	Intermediate Similarity	NPD6399	Phase 3
0.7024	Intermediate Similarity	NPD7514	Phase 3
0.7024	Intermediate Similarity	NPD7332	Phase 2
0.7024	Intermediate Similarity	NPD4695	Discontinued
0.7021	Intermediate Similarity	NPD4225	Approved
0.7011	Intermediate Similarity	NPD6893	Approved
0.7011	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5221	Approved
0.6989	Remote Similarity	NPD5222	Approved
0.6989	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4697	Phase 3
0.6941	Remote Similarity	NPD6902	Approved
0.6941	Remote Similarity	NPD6898	Phase 1
0.6932	Remote Similarity	NPD5279	Phase 3
0.6915	Remote Similarity	NPD7902	Approved
0.6915	Remote Similarity	NPD5173	Approved
0.6915	Remote Similarity	NPD4755	Approved
0.6905	Remote Similarity	NPD4195	Approved
0.6854	Remote Similarity	NPD7750	Discontinued
0.6842	Remote Similarity	NPD7638	Approved
0.6842	Remote Similarity	NPD5290	Discontinued
0.68	Remote Similarity	NPD368	Approved
0.6771	Remote Similarity	NPD5285	Approved
0.6771	Remote Similarity	NPD7639	Approved
0.6771	Remote Similarity	NPD4696	Approved
0.6771	Remote Similarity	NPD4700	Approved
0.6771	Remote Similarity	NPD7640	Approved
0.6771	Remote Similarity	NPD5286	Approved
0.6739	Remote Similarity	NPD6411	Approved
0.6703	Remote Similarity	NPD4753	Phase 2
0.6701	Remote Similarity	NPD5223	Approved
0.6701	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6633	Remote Similarity	NPD5226	Approved
0.6633	Remote Similarity	NPD5224	Approved
0.6633	Remote Similarity	NPD5211	Phase 2
0.6633	Remote Similarity	NPD5225	Approved
0.6633	Remote Similarity	NPD4633	Approved
0.6629	Remote Similarity	NPD5329	Approved
0.6628	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5739	Approved
0.66	Remote Similarity	NPD6402	Approved
0.66	Remote Similarity	NPD7128	Approved
0.66	Remote Similarity	NPD6675	Approved
0.6596	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7900	Approved
0.6566	Remote Similarity	NPD5174	Approved
0.6566	Remote Similarity	NPD5175	Approved
0.6566	Remote Similarity	NPD4754	Approved
0.6559	Remote Similarity	NPD7087	Discontinued
0.6556	Remote Similarity	NPD7521	Approved
0.6556	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7334	Approved
0.6556	Remote Similarity	NPD5330	Approved
0.6556	Remote Similarity	NPD6409	Approved
0.6556	Remote Similarity	NPD6684	Approved
0.6556	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6101	Approved
0.6517	Remote Similarity	NPD4197	Approved
0.6505	Remote Similarity	NPD4634	Approved
0.65	Remote Similarity	NPD5141	Approved
0.6471	Remote Similarity	NPD6899	Approved
0.6471	Remote Similarity	NPD7320	Approved
0.6471	Remote Similarity	NPD6881	Approved
0.6449	Remote Similarity	NPD7115	Discovery
0.6438	Remote Similarity	NPD342	Phase 1
0.6436	Remote Similarity	NPD4768	Approved
0.6436	Remote Similarity	NPD4767	Approved
0.6413	Remote Similarity	NPD6903	Approved
0.6413	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6373	Approved
0.6408	Remote Similarity	NPD6372	Approved
0.6404	Remote Similarity	NPD4788	Approved
0.6395	Remote Similarity	NPD3617	Approved
0.6392	Remote Similarity	NPD6084	Phase 2
0.6392	Remote Similarity	NPD6083	Phase 2
0.6383	Remote Similarity	NPD8035	Phase 2
0.6383	Remote Similarity	NPD8034	Phase 2
0.6381	Remote Similarity	NPD8297	Approved
0.6374	Remote Similarity	NPD4690	Approved
0.6374	Remote Similarity	NPD4693	Phase 3
0.6374	Remote Similarity	NPD4138	Approved
0.6374	Remote Similarity	NPD4689	Approved
0.6374	Remote Similarity	NPD4688	Approved
0.6374	Remote Similarity	NPD4519	Discontinued
0.6374	Remote Similarity	NPD5205	Approved
0.6374	Remote Similarity	NPD4623	Approved
0.6373	Remote Similarity	NPD5697	Approved
0.6373	Remote Similarity	NPD5701	Approved
0.6373	Remote Similarity	NPD6412	Phase 2
0.6354	Remote Similarity	NPD5210	Approved
0.6354	Remote Similarity	NPD4629	Approved
0.6346	Remote Similarity	NPD7290	Approved
0.6346	Remote Similarity	NPD7102	Approved
0.6346	Remote Similarity	NPD6883	Approved
0.6344	Remote Similarity	NPD6051	Approved
0.6344	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4787	Phase 1
0.6321	Remote Similarity	NPD4632	Approved
0.6311	Remote Similarity	NPD5168	Approved
0.6311	Remote Similarity	NPD5128	Approved
0.6311	Remote Similarity	NPD4729	Approved
0.6311	Remote Similarity	NPD4730	Approved
0.6311	Remote Similarity	NPD6011	Approved
0.6304	Remote Similarity	NPD3573	Approved
0.6286	Remote Similarity	NPD6649	Approved
0.6286	Remote Similarity	NPD6847	Approved
0.6286	Remote Similarity	NPD6617	Approved
0.6286	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6869	Approved
0.6286	Remote Similarity	NPD6650	Approved
0.6286	Remote Similarity	NPD8130	Phase 1
0.6277	Remote Similarity	NPD7136	Phase 2
0.6265	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6013	Approved
0.6237	Remote Similarity	NPD4723	Approved
0.6237	Remote Similarity	NPD6672	Approved
0.6237	Remote Similarity	NPD4722	Approved
0.6237	Remote Similarity	NPD5737	Approved
0.6226	Remote Similarity	NPD6882	Approved
0.622	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7637	Suspended
0.62	Remote Similarity	NPD5344	Discontinued
0.6196	Remote Similarity	NPD5690	Phase 2
0.6196	Remote Similarity	NPD4694	Approved
0.6196	Remote Similarity	NPD5280	Approved
0.619	Remote Similarity	NPD5169	Approved
0.619	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5251	Approved
0.619	Remote Similarity	NPD5135	Approved
0.619	Remote Similarity	NPD5247	Approved
0.619	Remote Similarity	NPD5248	Approved
0.619	Remote Similarity	NPD5249	Phase 3
0.619	Remote Similarity	NPD5250	Approved
0.6163	Remote Similarity	NPD6117	Approved
0.6154	Remote Similarity	NPD6686	Approved
0.6146	Remote Similarity	NPD5779	Approved
0.6146	Remote Similarity	NPD5778	Approved
0.6139	Remote Similarity	NPD7632	Discontinued
0.6133	Remote Similarity	NPD4219	Approved
0.6132	Remote Similarity	NPD5127	Approved
0.6132	Remote Similarity	NPD5215	Approved
0.6132	Remote Similarity	NPD5216	Approved
0.6132	Remote Similarity	NPD5217	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