NPASS Compound

Structure

NPC471799 OpenBabel07101718312D 22 24 0 0 1 0 0 0 0 0999 V2000 5.5549 2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1235 0.8912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5889 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 1.7321 -1.0000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 19 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 8 9 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 6 0 0 0 15 7 1 6 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 6 0 0 0 19 4 1 1 0 0 0 20 13 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	341.114
LogP:	4.33
LogD:	3.679
LogS:	-4.312
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	4.851
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.655
MDCK Permeability:	1.2533546396298334e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.919
30% Bioavailability (F30%):	0.401

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.389
Plasma Protein Binding (PPB):	94.44107818603516%
Volume Distribution (VD):	1.197
Pgp-substrate:	5.738509178161621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.084
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.155
CYP2C9-substrate:	0.243
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.874
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	6.918
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.331
Carcinogencity:	0.265
Eye Corrosion:	0.064
Eye Irritation:	0.302
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC471799

Natural Product ID:	NPC471799
*Common Name:**	(3S,5R,8R,9S,13R)-3,20-Dihydroxy-1(10),15-Rosadiene
IUPAC Name:	(2S,4bS,7R,8aR,10aR)-7-ethenyl-4b-(hydroxymethyl)-1,1,7-trimethyl-3,5,6,8,8a,9,10,10a-octahydro-2H-phenanthren-2-ol
Synonyms:
Standard InCHIKey:	XHDDXJBGGUJQQL-XUMMFJMYSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-5-19(4)10-11-20(13-21)14(12-19)6-7-15-16(20)8-9-17(22)18(15,2)3/h5,8,14-15,17,21-22H,1,6-7,9-13H2,2-4H3/t14-,15-,17+,19-,20+/m1/s1
SMILES:	CC1(C2CCC3CC(CCC3(C2=CCC1O)CO)(C)C=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234216
PubChem CID:	90670339
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[24660966]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29148766]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184480]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5570.0	nM	PMID[515611]

☑ 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 NPC471799 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	168
0.1-0.2	1269
0.2-0.3	6447
0.3-0.4	16070
0.4-0.5	8222
0.5-0.6	5920
0.6-0.7	3244
0.7-0.8	1075
0.8-0.85	165
0.85-0.9	88
0.9-0.95	25
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9853	High Similarity	NPC471797
0.9565	High Similarity	NPC477138
0.9565	High Similarity	NPC243342
0.9559	High Similarity	NPC242001
0.9437	High Similarity	NPC471798
0.9429	High Similarity	NPC291503
0.942	High Similarity	NPC182717
0.9412	High Similarity	NPC145498
0.9403	High Similarity	NPC208999
0.9306	High Similarity	NPC167891
0.9306	High Similarity	NPC83351
0.9296	High Similarity	NPC107059
0.9296	High Similarity	NPC321016
0.9296	High Similarity	NPC113733
0.9296	High Similarity	NPC321381
0.9286	High Similarity	NPC91858
0.9254	High Similarity	NPC197805
0.9167	High Similarity	NPC318495
0.9167	High Similarity	NPC91594
0.9167	High Similarity	NPC155986
0.9167	High Similarity	NPC198968
0.9155	High Similarity	NPC28657
0.9155	High Similarity	NPC285893
0.9155	High Similarity	NPC162742
0.9155	High Similarity	NPC136188
0.9155	High Similarity	NPC230301
0.9155	High Similarity	NPC304309
0.9155	High Similarity	NPC22105
0.9155	High Similarity	NPC288035
0.9155	High Similarity	NPC477923
0.9155	High Similarity	NPC134847
0.9155	High Similarity	NPC66566
0.9104	High Similarity	NPC476039
0.9104	High Similarity	NPC286669
0.9104	High Similarity	NPC222366
0.9054	High Similarity	NPC164840
0.9054	High Similarity	NPC241290
0.9054	High Similarity	NPC234193
0.9054	High Similarity	NPC209944
0.9041	High Similarity	NPC22955
0.9041	High Similarity	NPC474216
0.9041	High Similarity	NPC470396
0.9041	High Similarity	NPC99168
0.9041	High Similarity	NPC76931
0.9041	High Similarity	NPC474989
0.9041	High Similarity	NPC473943
0.9041	High Similarity	NPC18603
0.9041	High Similarity	NPC477522
0.9041	High Similarity	NPC87604
0.9041	High Similarity	NPC307965
0.9028	High Similarity	NPC274079
0.9028	High Similarity	NPC477925
0.9028	High Similarity	NPC265588
0.9028	High Similarity	NPC240604
0.9028	High Similarity	NPC106432
0.9028	High Similarity	NPC96319
0.9028	High Similarity	NPC106364
0.9028	High Similarity	NPC134330
0.9028	High Similarity	NPC300324
0.9028	High Similarity	NPC129165
0.9014	High Similarity	NPC100334
0.9	High Similarity	NPC167706
0.9	High Similarity	NPC110799
0.8933	High Similarity	NPC264245
0.8933	High Similarity	NPC476646
0.8933	High Similarity	NPC47761
0.8919	High Similarity	NPC53744
0.8919	High Similarity	NPC328714
0.8919	High Similarity	NPC84694
0.8919	High Similarity	NPC109546
0.8919	High Similarity	NPC81306
0.8919	High Similarity	NPC143182
0.8919	High Similarity	NPC28862
0.8919	High Similarity	NPC47982
0.8919	High Similarity	NPC291379
0.8904	High Similarity	NPC472805
0.8904	High Similarity	NPC477924
0.8904	High Similarity	NPC90979
0.8904	High Similarity	NPC157996
0.8904	High Similarity	NPC34019
0.8904	High Similarity	NPC101475
0.8904	High Similarity	NPC40394
0.8904	High Similarity	NPC34177
0.8889	High Similarity	NPC257347
0.8889	High Similarity	NPC141071
0.8889	High Similarity	NPC471723
0.8873	High Similarity	NPC68443
0.8857	High Similarity	NPC34834
0.8857	High Similarity	NPC92801
0.8841	High Similarity	NPC32055
0.8816	High Similarity	NPC50964
0.8816	High Similarity	NPC49964
0.8806	High Similarity	NPC290367
0.88	High Similarity	NPC26117
0.88	High Similarity	NPC96362
0.88	High Similarity	NPC287749
0.8784	High Similarity	NPC300499
0.8784	High Similarity	NPC253807
0.8784	High Similarity	NPC196753
0.8784	High Similarity	NPC476314
0.8784	High Similarity	NPC275910
0.8784	High Similarity	NPC158662
0.8784	High Similarity	NPC230295
0.8784	High Similarity	NPC98386
0.8767	High Similarity	NPC30590
0.8767	High Similarity	NPC265328
0.8767	High Similarity	NPC470362
0.8767	High Similarity	NPC290598
0.8767	High Similarity	NPC122418
0.8767	High Similarity	NPC253190
0.8767	High Similarity	NPC120098
0.8767	High Similarity	NPC27765
0.8767	High Similarity	NPC189883
0.8701	High Similarity	NPC237795
0.8701	High Similarity	NPC82538
0.8684	High Similarity	NPC142163
0.8684	High Similarity	NPC474731
0.8684	High Similarity	NPC470383
0.8684	High Similarity	NPC82986
0.8684	High Similarity	NPC474531
0.8684	High Similarity	NPC23852
0.8684	High Similarity	NPC474683
0.8684	High Similarity	NPC474752
0.8684	High Similarity	NPC7505
0.8684	High Similarity	NPC209620
0.8684	High Similarity	NPC474759
0.8676	High Similarity	NPC163678
0.8667	High Similarity	NPC100906
0.8667	High Similarity	NPC30986
0.8667	High Similarity	NPC472463
0.8667	High Similarity	NPC1319
0.8667	High Similarity	NPC209430
0.8649	High Similarity	NPC470711
0.8649	High Similarity	NPC470758
0.8649	High Similarity	NPC130136
0.8649	High Similarity	NPC214570
0.863	High Similarity	NPC138374
0.863	High Similarity	NPC34700
0.8611	High Similarity	NPC474140
0.859	High Similarity	NPC205845
0.859	High Similarity	NPC33913
0.8571	High Similarity	NPC470614
0.8571	High Similarity	NPC1272
0.8571	High Similarity	NPC189972
0.8571	High Similarity	NPC101462
0.8571	High Similarity	NPC248886
0.8571	High Similarity	NPC216460
0.8571	High Similarity	NPC5985
0.8553	High Similarity	NPC236112
0.8553	High Similarity	NPC295131
0.8551	High Similarity	NPC149680
0.8533	High Similarity	NPC148977
0.8533	High Similarity	NPC11908
0.8533	High Similarity	NPC477514
0.8533	High Similarity	NPC6978
0.8533	High Similarity	NPC244385
0.8533	High Similarity	NPC285761
0.8533	High Similarity	NPC167037
0.8533	High Similarity	NPC72507
0.8533	High Similarity	NPC138621
0.8514	High Similarity	NPC247325
0.8514	High Similarity	NPC237460
0.8514	High Similarity	NPC202642
0.8514	High Similarity	NPC470749
0.8514	High Similarity	NPC73875
0.8514	High Similarity	NPC244488
0.8514	High Similarity	NPC46160
0.8493	Intermediate Similarity	NPC469534
0.8493	Intermediate Similarity	NPC201048
0.8493	Intermediate Similarity	NPC469593
0.8493	Intermediate Similarity	NPC476366
0.8493	Intermediate Similarity	NPC469533
0.8493	Intermediate Similarity	NPC306727
0.8481	Intermediate Similarity	NPC157257
0.8481	Intermediate Similarity	NPC274448
0.8472	Intermediate Similarity	NPC164022
0.8462	Intermediate Similarity	NPC474634
0.8462	Intermediate Similarity	NPC475789
0.8462	Intermediate Similarity	NPC317458
0.8451	Intermediate Similarity	NPC471560
0.8451	Intermediate Similarity	NPC9942
0.8451	Intermediate Similarity	NPC210323
0.8442	Intermediate Similarity	NPC249423
0.8442	Intermediate Similarity	NPC242350
0.8442	Intermediate Similarity	NPC14151
0.8442	Intermediate Similarity	NPC116202
0.8429	Intermediate Similarity	NPC69649
0.8429	Intermediate Similarity	NPC114651
0.8429	Intermediate Similarity	NPC68703
0.8421	Intermediate Similarity	NPC80530
0.8421	Intermediate Similarity	NPC273410
0.8378	Intermediate Similarity	NPC471468
0.8378	Intermediate Similarity	NPC322353
0.8378	Intermediate Similarity	NPC121744
0.8378	Intermediate Similarity	NPC118508
0.8375	Intermediate Similarity	NPC261266
0.8354	Intermediate Similarity	NPC59453
0.8354	Intermediate Similarity	NPC470077
0.8354	Intermediate Similarity	NPC474493
0.8354	Intermediate Similarity	NPC185568

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 NPC471799 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1524
0.2-0.3	4136
0.3-0.4	2308
0.4-0.5	614
0.5-0.6	204
0.6-0.7	153
0.7-0.8	49
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9155	High Similarity	NPD7339	Approved
0.9155	High Similarity	NPD6942	Approved
0.9028	High Similarity	NPD3701	Clinical (unspecified phase)
0.8667	High Similarity	NPD7645	Phase 2
0.8354	Intermediate Similarity	NPD4786	Approved
0.8333	Intermediate Similarity	NPD3667	Approved
0.8312	Intermediate Similarity	NPD7525	Registered
0.8243	Intermediate Similarity	NPD6924	Approved
0.8243	Intermediate Similarity	NPD4785	Approved
0.8243	Intermediate Similarity	NPD4784	Approved
0.8243	Intermediate Similarity	NPD6926	Approved
0.8219	Intermediate Similarity	NPD7151	Approved
0.8219	Intermediate Similarity	NPD7152	Approved
0.8219	Intermediate Similarity	NPD7150	Approved
0.8133	Intermediate Similarity	NPD8264	Approved
0.8082	Intermediate Similarity	NPD7143	Approved
0.8082	Intermediate Similarity	NPD7144	Approved
0.8026	Intermediate Similarity	NPD6933	Approved
0.7973	Intermediate Similarity	NPD4243	Approved
0.7945	Intermediate Similarity	NPD6923	Approved
0.7945	Intermediate Similarity	NPD6922	Approved
0.7831	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6929	Approved
0.7711	Intermediate Similarity	NPD3618	Phase 1
0.7692	Intermediate Similarity	NPD6932	Approved
0.7683	Intermediate Similarity	NPD3665	Phase 1
0.7683	Intermediate Similarity	NPD3133	Approved
0.7683	Intermediate Similarity	NPD3666	Approved
0.7674	Intermediate Similarity	NPD6079	Approved
0.7647	Intermediate Similarity	NPD5328	Approved
0.7625	Intermediate Similarity	NPD6930	Phase 2
0.7625	Intermediate Similarity	NPD7509	Discontinued
0.7625	Intermediate Similarity	NPD6931	Approved
0.7625	Intermediate Similarity	NPD4748	Discontinued
0.7595	Intermediate Similarity	NPD7145	Approved
0.7595	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4195	Approved
0.7471	Intermediate Similarity	NPD7515	Phase 2
0.747	Intermediate Similarity	NPD3668	Phase 3
0.7468	Intermediate Similarity	NPD6925	Approved
0.7468	Intermediate Similarity	NPD5776	Phase 2
0.7436	Intermediate Similarity	NPD5275	Approved
0.7436	Intermediate Similarity	NPD4190	Phase 3
0.7407	Intermediate Similarity	NPD7332	Phase 2
0.7407	Intermediate Similarity	NPD7514	Phase 3
0.7386	Intermediate Similarity	NPD6399	Phase 3
0.7349	Intermediate Similarity	NPD6695	Phase 3
0.7317	Intermediate Similarity	NPD6902	Approved
0.7284	Intermediate Similarity	NPD6683	Phase 2
0.7262	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4695	Discontinued
0.7191	Intermediate Similarity	NPD4202	Approved
0.7176	Intermediate Similarity	NPD6893	Approved
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7748	Approved
0.7108	Intermediate Similarity	NPD6898	Phase 1
0.7093	Intermediate Similarity	NPD5279	Phase 3
0.7065	Intermediate Similarity	NPD5173	Approved
0.7045	Intermediate Similarity	NPD4753	Phase 2
0.7024	Intermediate Similarity	NPD4223	Phase 3
0.7024	Intermediate Similarity	NPD4221	Approved
0.7011	Intermediate Similarity	NPD7750	Discontinued
0.7011	Intermediate Similarity	NPD7524	Approved
0.6989	Remote Similarity	NPD5290	Discontinued
0.6986	Remote Similarity	NPD368	Approved
0.6977	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5329	Approved
0.6957	Remote Similarity	NPD4697	Phase 3
0.6915	Remote Similarity	NPD5285	Approved
0.6915	Remote Similarity	NPD5286	Approved
0.6915	Remote Similarity	NPD4696	Approved
0.6897	Remote Similarity	NPD4519	Discontinued
0.6897	Remote Similarity	NPD7334	Approved
0.6897	Remote Similarity	NPD7146	Approved
0.6897	Remote Similarity	NPD5330	Approved
0.6897	Remote Similarity	NPD6684	Approved
0.6897	Remote Similarity	NPD6409	Approved
0.6897	Remote Similarity	NPD7521	Approved
0.6897	Remote Similarity	NPD4623	Approved
0.6889	Remote Similarity	NPD6411	Approved
0.6882	Remote Similarity	NPD4755	Approved
0.6882	Remote Similarity	NPD7902	Approved
0.686	Remote Similarity	NPD4197	Approved
0.6857	Remote Similarity	NPD342	Phase 1
0.6848	Remote Similarity	NPD4629	Approved
0.6848	Remote Similarity	NPD5210	Approved
0.6842	Remote Similarity	NPD5223	Approved
0.6809	Remote Similarity	NPD7638	Approved
0.6786	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4633	Approved
0.6771	Remote Similarity	NPD5224	Approved
0.6771	Remote Similarity	NPD5211	Phase 2
0.6771	Remote Similarity	NPD5226	Approved
0.6771	Remote Similarity	NPD5225	Approved
0.6747	Remote Similarity	NPD3617	Approved
0.6744	Remote Similarity	NPD4788	Approved
0.6742	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6903	Approved
0.6737	Remote Similarity	NPD7639	Approved
0.6737	Remote Similarity	NPD7640	Approved
0.6737	Remote Similarity	NPD4700	Approved
0.6705	Remote Similarity	NPD4693	Phase 3
0.6705	Remote Similarity	NPD4688	Approved
0.6705	Remote Similarity	NPD4690	Approved
0.6705	Remote Similarity	NPD4689	Approved
0.6705	Remote Similarity	NPD5690	Phase 2
0.6705	Remote Similarity	NPD5205	Approved
0.6705	Remote Similarity	NPD4138	Approved
0.6703	Remote Similarity	NPD7087	Discontinued
0.6702	Remote Similarity	NPD6083	Phase 2
0.6702	Remote Similarity	NPD6084	Phase 2
0.6701	Remote Similarity	NPD5174	Approved
0.6701	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6633	Remote Similarity	NPD5141	Approved
0.66	Remote Similarity	NPD6881	Approved
0.66	Remote Similarity	NPD6899	Approved
0.6593	Remote Similarity	NPD7136	Phase 2
0.6582	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6675	Approved
0.6566	Remote Similarity	NPD5739	Approved
0.6566	Remote Similarity	NPD6402	Approved
0.6566	Remote Similarity	NPD7128	Approved
0.6559	Remote Similarity	NPD7900	Approved
0.6559	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6672	Approved
0.6556	Remote Similarity	NPD4723	Approved
0.6556	Remote Similarity	NPD5737	Approved
0.6556	Remote Similarity	NPD4722	Approved
0.6531	Remote Similarity	NPD4754	Approved
0.6528	Remote Similarity	NPD4219	Approved
0.6522	Remote Similarity	NPD7637	Suspended
0.6517	Remote Similarity	NPD4694	Approved
0.6517	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5280	Approved
0.65	Remote Similarity	NPD5697	Approved
0.65	Remote Similarity	NPD4787	Phase 1
0.6471	Remote Similarity	NPD7290	Approved
0.6471	Remote Similarity	NPD7102	Approved
0.6471	Remote Similarity	NPD6883	Approved
0.6458	Remote Similarity	NPD4225	Approved
0.6444	Remote Similarity	NPD3573	Approved
0.6436	Remote Similarity	NPD6011	Approved
0.6436	Remote Similarity	NPD5168	Approved
0.6436	Remote Similarity	NPD4729	Approved
0.6436	Remote Similarity	NPD4730	Approved
0.6436	Remote Similarity	NPD7320	Approved
0.642	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6869	Approved
0.6408	Remote Similarity	NPD8130	Phase 1
0.6408	Remote Similarity	NPD6847	Approved
0.6408	Remote Similarity	NPD6649	Approved
0.6408	Remote Similarity	NPD6650	Approved
0.6408	Remote Similarity	NPD6617	Approved
0.64	Remote Similarity	NPD4768	Approved
0.64	Remote Similarity	NPD4767	Approved
0.6375	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD4137	Phase 3
0.6373	Remote Similarity	NPD6014	Approved
0.6373	Remote Similarity	NPD6012	Approved
0.6373	Remote Similarity	NPD6373	Approved
0.6373	Remote Similarity	NPD6372	Approved
0.6373	Remote Similarity	NPD6013	Approved
0.6346	Remote Similarity	NPD8297	Approved
0.6346	Remote Similarity	NPD6882	Approved
0.6344	Remote Similarity	NPD5281	Approved
0.6344	Remote Similarity	NPD8034	Phase 2
0.6344	Remote Similarity	NPD8035	Phase 2
0.6344	Remote Similarity	NPD5284	Approved
0.6341	Remote Similarity	NPD4732	Discontinued
0.6337	Remote Similarity	NPD6412	Phase 2
0.6337	Remote Similarity	NPD5701	Approved
0.6333	Remote Similarity	NPD6098	Approved
0.6327	Remote Similarity	NPD4159	Approved
0.6322	Remote Similarity	NPD4692	Approved
0.6322	Remote Similarity	NPD4139	Approved
0.6316	Remote Similarity	NPD5695	Phase 3
0.6311	Remote Similarity	NPD5135	Approved
0.6311	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5251	Approved
0.6311	Remote Similarity	NPD5248	Approved
0.6311	Remote Similarity	NPD5250	Approved
0.6311	Remote Similarity	NPD4634	Approved
0.6311	Remote Similarity	NPD5249	Phase 3
0.6311	Remote Similarity	NPD5169	Approved
0.6311	Remote Similarity	NPD5247	Approved
0.6296	Remote Similarity	NPD4691	Approved
0.6296	Remote Similarity	NPD4244	Approved
0.6296	Remote Similarity	NPD4245	Approved
0.6296	Remote Similarity	NPD4747	Approved
0.6289	Remote Similarity	NPD5696	Approved
0.6277	Remote Similarity	NPD5779	Approved
0.6277	Remote Similarity	NPD5778	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