NPASS Compound

Structure

NPC32055 OpenBabel07101719512D 21 23 0 0 1 0 0 0 0 0999 V2000 -3.4641 3.0000 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 0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 1.7321 -0.0000 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 -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 -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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 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 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 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 -0.0000 -1.0000 0.0000 C 0 0 1 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3660 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 14 1 0 0 0 0 5 15 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 16 8 1 1 0 0 0 16 17 1 0 0 0 0 17 20 1 6 0 0 0 18 19 1 6 0 0 0 18 20 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	332.324
LogP:	5.134
LogD:	4.462
LogS:	-5.222
# Rotatable Bonds:	2
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	4.362
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:	-4.766
MDCK Permeability:	1.2419177437550388e-05
Pgp-inhibitor:	0.584
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.552

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	95.40348052978516%
Volume Distribution (VD):	1.6
Pgp-substrate:	1.9092427492141724%

ADMET: Metabolism

CYP1A2-inhibitor:	0.395
CYP1A2-substrate:	0.646
CYP2C19-inhibitor:	0.175
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.244
CYP2C9-substrate:	0.132
CYP2D6-inhibitor:	0.633
CYP2D6-substrate:	0.631
CYP3A4-inhibitor:	0.89
CYP3A4-substrate:	0.686

ADMET: Excretion

Clearance (CL):	6.804
Half-life (T1/2):	0.363

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.528
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.42
Skin Sensitization:	0.95
Carcinogencity:	0.049
Eye Corrosion:	0.96
Eye Irritation:	0.945
Respiratory Toxicity:	0.806

Download Data

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

Natural Product: NPC32055

Natural Product ID:	NPC32055
*Common Name:**	18-Hydroxycassan-13,15-Diene
IUPAC Name:	[(1R,4aR,4bS,8aR,10aR)-7-ethenyl-1,4a,8-trimethyl-2,3,4,4b,5,6,8a,9,10,10a-decahydrophenanthren-1-yl]methanol
Synonyms:
Standard InCHIKey:	XMNZLNUFQJDGKT-VYJAJWGXSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-5-15-7-9-17-16(14(15)2)8-10-18-19(3,13-21)11-6-12-20(17,18)4/h5,16-18,21H,1,6-13H2,2-4H3/t16-,17-,18-,19-,20+/m0/s1
SMILES:	C=CC1=C(C)[C@@H]2CC[C@H]3[C@@](C)(CCC[C@]3(C)[C@H]2CC1)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457953
PubChem CID:	21674167
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002550] Isocopalane and spongiane 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
NPO10318	Myrospermum frutescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880308]
NPO10318	Myrospermum frutescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497945]
NPO10318	Myrospermum frutescens	Species	Fabaceae	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
Others	1

Activity Type	# Activity
Cell Line	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT859	Cell Line	HFF	Homo sapiens	IC50	=	149000.0	nM	PMID[506923]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	17000.0	nM	PMID[506922]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	48000.0	nM	PMID[506922]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	48600.0	nM	PMID[506923]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	17400.0	nM	PMID[506923]
NPT2	Others	Unspecified		Ratio IC50	=	9.0	n.a.	PMID[506923]

☑ 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 NPC32055 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	177
0.1-0.2	1414
0.2-0.3	8387
0.3-0.4	16626
0.4-0.5	7852
0.5-0.6	5416
0.6-0.7	2216
0.7-0.8	511
0.8-0.85	72
0.85-0.9	19
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9531	High Similarity	NPC197805
0.9385	High Similarity	NPC216460
0.9375	High Similarity	NPC476039
0.9375	High Similarity	NPC222366
0.9375	High Similarity	NPC286669
0.9375	High Similarity	NPC149680
0.9219	High Similarity	NPC163678
0.9	High Similarity	NPC106432
0.8857	High Similarity	NPC471468
0.8841	High Similarity	NPC471799
0.8841	High Similarity	NPC182717
0.8824	High Similarity	NPC145498
0.875	High Similarity	NPC307965
0.875	High Similarity	NPC18603
0.875	High Similarity	NPC76931
0.8714	High Similarity	NPC471797
0.8696	High Similarity	NPC242001
0.8696	High Similarity	NPC110799
0.8571	High Similarity	NPC68443
0.8529	High Similarity	NPC160209
0.8529	High Similarity	NPC208999
0.8493	Intermediate Similarity	NPC72507
0.8472	Intermediate Similarity	NPC134330
0.8472	Intermediate Similarity	NPC129165
0.8472	Intermediate Similarity	NPC113733
0.8451	Intermediate Similarity	NPC91858
0.8451	Intermediate Similarity	NPC477138
0.8451	Intermediate Similarity	NPC100334
0.8451	Intermediate Similarity	NPC243342
0.8406	Intermediate Similarity	NPC476431
0.8382	Intermediate Similarity	NPC68703
0.8382	Intermediate Similarity	NPC69649
0.8378	Intermediate Similarity	NPC474113
0.8356	Intermediate Similarity	NPC91594
0.8356	Intermediate Similarity	NPC471798
0.8333	Intermediate Similarity	NPC291503
0.8333	Intermediate Similarity	NPC285893
0.8333	Intermediate Similarity	NPC28657
0.8333	Intermediate Similarity	NPC471723
0.8333	Intermediate Similarity	NPC138374
0.8333	Intermediate Similarity	NPC136188
0.8333	Intermediate Similarity	NPC34700
0.8333	Intermediate Similarity	NPC22105
0.8333	Intermediate Similarity	NPC162742
0.8333	Intermediate Similarity	NPC257347
0.8333	Intermediate Similarity	NPC288035
0.8333	Intermediate Similarity	NPC230301
0.8333	Intermediate Similarity	NPC304309
0.8333	Intermediate Similarity	NPC134847
0.8333	Intermediate Similarity	NPC141071
0.831	Intermediate Similarity	NPC474743
0.831	Intermediate Similarity	NPC130665
0.8286	Intermediate Similarity	NPC475728
0.8286	Intermediate Similarity	NPC34834
0.8243	Intermediate Similarity	NPC205455
0.8243	Intermediate Similarity	NPC83351
0.8243	Intermediate Similarity	NPC186191
0.8243	Intermediate Similarity	NPC167891
0.8243	Intermediate Similarity	NPC318136
0.8235	Intermediate Similarity	NPC279434
0.8219	Intermediate Similarity	NPC290598
0.8219	Intermediate Similarity	NPC244488
0.8219	Intermediate Similarity	NPC122418
0.8219	Intermediate Similarity	NPC247325
0.8219	Intermediate Similarity	NPC27765
0.8219	Intermediate Similarity	NPC470362
0.8219	Intermediate Similarity	NPC30590
0.8219	Intermediate Similarity	NPC107059
0.8219	Intermediate Similarity	NPC265328
0.8219	Intermediate Similarity	NPC300324
0.8219	Intermediate Similarity	NPC240604
0.8219	Intermediate Similarity	NPC321381
0.8219	Intermediate Similarity	NPC321016
0.8219	Intermediate Similarity	NPC106364
0.8219	Intermediate Similarity	NPC189883
0.8219	Intermediate Similarity	NPC120098
0.8182	Intermediate Similarity	NPC52108
0.8182	Intermediate Similarity	NPC474789
0.8182	Intermediate Similarity	NPC237795
0.8182	Intermediate Similarity	NPC82538
0.8169	Intermediate Similarity	NPC167706
0.8116	Intermediate Similarity	NPC171225
0.8108	Intermediate Similarity	NPC472805
0.8108	Intermediate Similarity	NPC130136
0.8108	Intermediate Similarity	NPC157996
0.8108	Intermediate Similarity	NPC34019
0.8108	Intermediate Similarity	NPC198968
0.8108	Intermediate Similarity	NPC90979
0.8108	Intermediate Similarity	NPC101475
0.8108	Intermediate Similarity	NPC155986
0.8108	Intermediate Similarity	NPC318495
0.8108	Intermediate Similarity	NPC40394
0.8108	Intermediate Similarity	NPC34177
0.8088	Intermediate Similarity	NPC476737
0.8088	Intermediate Similarity	NPC27243
0.8082	Intermediate Similarity	NPC66566
0.8082	Intermediate Similarity	NPC477923
0.8056	Intermediate Similarity	NPC474140
0.8052	Intermediate Similarity	NPC20853
0.8028	Intermediate Similarity	NPC49422
0.8028	Intermediate Similarity	NPC9161
0.8026	Intermediate Similarity	NPC209944
0.8026	Intermediate Similarity	NPC234193
0.8026	Intermediate Similarity	NPC241290
0.8026	Intermediate Similarity	NPC164840
0.8	Intermediate Similarity	NPC477514
0.8	Intermediate Similarity	NPC2648
0.8	Intermediate Similarity	NPC196753
0.8	Intermediate Similarity	NPC253807
0.8	Intermediate Similarity	NPC99168
0.8	Intermediate Similarity	NPC230295
0.8	Intermediate Similarity	NPC474989
0.8	Intermediate Similarity	NPC158662
0.8	Intermediate Similarity	NPC470396
0.8	Intermediate Similarity	NPC87604
0.8	Intermediate Similarity	NPC473943
0.8	Intermediate Similarity	NPC477522
0.8	Intermediate Similarity	NPC98386
0.8	Intermediate Similarity	NPC474216
0.8	Intermediate Similarity	NPC22955
0.8	Intermediate Similarity	NPC94192
0.8	Intermediate Similarity	NPC300499
0.7973	Intermediate Similarity	NPC265588
0.7973	Intermediate Similarity	NPC274079
0.7973	Intermediate Similarity	NPC477925
0.7973	Intermediate Similarity	NPC46160
0.7973	Intermediate Similarity	NPC96319
0.7973	Intermediate Similarity	NPC253190
0.7973	Intermediate Similarity	NPC202642
0.7973	Intermediate Similarity	NPC470749
0.7973	Intermediate Similarity	NPC237460
0.7971	Intermediate Similarity	NPC476406
0.7949	Intermediate Similarity	NPC309309
0.7949	Intermediate Similarity	NPC291999
0.7949	Intermediate Similarity	NPC470384
0.7945	Intermediate Similarity	NPC469534
0.7945	Intermediate Similarity	NPC469533
0.7945	Intermediate Similarity	NPC329090
0.7945	Intermediate Similarity	NPC469593
0.7945	Intermediate Similarity	NPC476366
0.7945	Intermediate Similarity	NPC27395
0.7945	Intermediate Similarity	NPC201048
0.7941	Intermediate Similarity	NPC225415
0.7941	Intermediate Similarity	NPC290367
0.7922	Intermediate Similarity	NPC121984
0.7922	Intermediate Similarity	NPC6707
0.7922	Intermediate Similarity	NPC47761
0.7922	Intermediate Similarity	NPC264245
0.7922	Intermediate Similarity	NPC476646
0.7895	Intermediate Similarity	NPC30986
0.7895	Intermediate Similarity	NPC291379
0.7895	Intermediate Similarity	NPC81306
0.7895	Intermediate Similarity	NPC209430
0.7895	Intermediate Similarity	NPC100906
0.7895	Intermediate Similarity	NPC328714
0.7895	Intermediate Similarity	NPC28862
0.7895	Intermediate Similarity	NPC53744
0.7895	Intermediate Similarity	NPC1319
0.7895	Intermediate Similarity	NPC47982
0.7895	Intermediate Similarity	NPC143182
0.7895	Intermediate Similarity	NPC109546
0.7895	Intermediate Similarity	NPC84694
0.7887	Intermediate Similarity	NPC167272
0.7887	Intermediate Similarity	NPC269877
0.7887	Intermediate Similarity	NPC474248
0.7887	Intermediate Similarity	NPC210323
0.7887	Intermediate Similarity	NPC471560
0.7867	Intermediate Similarity	NPC470711
0.7867	Intermediate Similarity	NPC470758
0.7867	Intermediate Similarity	NPC477924
0.7867	Intermediate Similarity	NPC214570
0.7857	Intermediate Similarity	NPC114651
0.7848	Intermediate Similarity	NPC53385
0.7848	Intermediate Similarity	NPC474493
0.7848	Intermediate Similarity	NPC231310
0.7848	Intermediate Similarity	NPC238485
0.7838	Intermediate Similarity	NPC322353
0.7838	Intermediate Similarity	NPC328104
0.7838	Intermediate Similarity	NPC319090
0.7838	Intermediate Similarity	NPC118508
0.7838	Intermediate Similarity	NPC121744
0.7838	Intermediate Similarity	NPC32832
0.7826	Intermediate Similarity	NPC64123
0.7821	Intermediate Similarity	NPC50964
0.7821	Intermediate Similarity	NPC201852
0.7821	Intermediate Similarity	NPC202389
0.7821	Intermediate Similarity	NPC49964
0.7808	Intermediate Similarity	NPC201373
0.7792	Intermediate Similarity	NPC2482
0.7792	Intermediate Similarity	NPC295131
0.7792	Intermediate Similarity	NPC96362
0.7792	Intermediate Similarity	NPC26117
0.7792	Intermediate Similarity	NPC287749
0.7792	Intermediate Similarity	NPC236112
0.7778	Intermediate Similarity	NPC92801
0.7763	Intermediate Similarity	NPC275910
0.7763	Intermediate Similarity	NPC65897
0.7763	Intermediate Similarity	NPC148977
0.7763	Intermediate Similarity	NPC85346
0.7763	Intermediate Similarity	NPC244385

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 NPC32055 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1626
0.2-0.3	4267
0.3-0.4	2195
0.4-0.5	545
0.5-0.6	211
0.6-0.7	93
0.7-0.8	35
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD6942	Approved
0.8333	Intermediate Similarity	NPD7339	Approved
0.8028	Intermediate Similarity	NPD7143	Approved
0.8028	Intermediate Similarity	NPD7144	Approved
0.7973	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD6926	Approved
0.7945	Intermediate Similarity	NPD4785	Approved
0.7945	Intermediate Similarity	NPD6924	Approved
0.7945	Intermediate Similarity	NPD4784	Approved
0.7917	Intermediate Similarity	NPD7150	Approved
0.7917	Intermediate Similarity	NPD7151	Approved
0.7917	Intermediate Similarity	NPD4243	Approved
0.7917	Intermediate Similarity	NPD7152	Approved
0.7895	Intermediate Similarity	NPD7645	Phase 2
0.7887	Intermediate Similarity	NPD6923	Approved
0.7887	Intermediate Similarity	NPD6922	Approved
0.7733	Intermediate Similarity	NPD6933	Approved
0.76	Intermediate Similarity	NPD8264	Approved
0.7564	Intermediate Similarity	NPD7525	Registered
0.7436	Intermediate Similarity	NPD6929	Approved
0.7407	Intermediate Similarity	NPD4786	Approved
0.7403	Intermediate Similarity	NPD6932	Approved
0.7375	Intermediate Similarity	NPD3667	Approved
0.7368	Intermediate Similarity	NPD4190	Phase 3
0.7368	Intermediate Similarity	NPD5275	Approved
0.7342	Intermediate Similarity	NPD6930	Phase 2
0.7342	Intermediate Similarity	NPD7509	Discontinued
0.7342	Intermediate Similarity	NPD6931	Approved
0.7308	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7145	Approved
0.7215	Intermediate Similarity	NPD4195	Approved
0.7195	Intermediate Similarity	NPD3665	Phase 1
0.7195	Intermediate Similarity	NPD3133	Approved
0.7195	Intermediate Similarity	NPD3666	Approved
0.7179	Intermediate Similarity	NPD5776	Phase 2
0.7179	Intermediate Similarity	NPD6925	Approved
0.7164	Intermediate Similarity	NPD4219	Approved
0.7125	Intermediate Similarity	NPD7332	Phase 2
0.7125	Intermediate Similarity	NPD7514	Phase 3
0.7073	Intermediate Similarity	NPD6695	Phase 3
0.7037	Intermediate Similarity	NPD6902	Approved
0.7024	Intermediate Similarity	NPD3618	Phase 1
0.7024	Intermediate Similarity	NPD5279	Phase 3
0.7015	Intermediate Similarity	NPD342	Phase 1
0.7011	Intermediate Similarity	NPD6079	Approved
0.7	Intermediate Similarity	NPD6683	Phase 2
0.6988	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5328	Approved
0.6941	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4748	Discontinued
0.6905	Remote Similarity	NPD6893	Approved
0.6829	Remote Similarity	NPD6898	Phase 1
0.6818	Remote Similarity	NPD7515	Phase 2
0.6782	Remote Similarity	NPD4753	Phase 2
0.6782	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4223	Phase 3
0.6747	Remote Similarity	NPD4221	Approved
0.6744	Remote Similarity	NPD7750	Discontinued
0.6744	Remote Similarity	NPD7524	Approved
0.6707	Remote Similarity	NPD4695	Discontinued
0.6706	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6629	Remote Similarity	NPD6411	Approved
0.6628	Remote Similarity	NPD4519	Discontinued
0.6628	Remote Similarity	NPD5280	Approved
0.6628	Remote Similarity	NPD4623	Approved
0.6628	Remote Similarity	NPD4694	Approved
0.6593	Remote Similarity	NPD4629	Approved
0.6593	Remote Similarity	NPD5210	Approved
0.6588	Remote Similarity	NPD4197	Approved
0.6588	Remote Similarity	NPD3668	Phase 3
0.6556	Remote Similarity	NPD6399	Phase 3
0.6556	Remote Similarity	NPD4202	Approved
0.6522	Remote Similarity	NPD5221	Approved
0.6522	Remote Similarity	NPD5222	Approved
0.6522	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7748	Approved
0.6471	Remote Similarity	NPD4788	Approved
0.6452	Remote Similarity	NPD6083	Phase 2
0.6452	Remote Similarity	NPD6084	Phase 2
0.6452	Remote Similarity	NPD5173	Approved
0.6444	Remote Similarity	NPD7087	Discontinued
0.6444	Remote Similarity	NPD5281	Approved
0.6444	Remote Similarity	NPD5284	Approved
0.6438	Remote Similarity	NPD368	Approved
0.6437	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5205	Approved
0.6437	Remote Similarity	NPD5330	Approved
0.6437	Remote Similarity	NPD4693	Phase 3
0.6437	Remote Similarity	NPD7521	Approved
0.6437	Remote Similarity	NPD4689	Approved
0.6437	Remote Similarity	NPD5690	Phase 2
0.6437	Remote Similarity	NPD4688	Approved
0.6437	Remote Similarity	NPD7334	Approved
0.6437	Remote Similarity	NPD6409	Approved
0.6437	Remote Similarity	NPD6684	Approved
0.6437	Remote Similarity	NPD7146	Approved
0.6437	Remote Similarity	NPD4690	Approved
0.6437	Remote Similarity	NPD4138	Approved
0.6404	Remote Similarity	NPD6101	Approved
0.6404	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5290	Discontinued
0.6375	Remote Similarity	NPD4058	Approved
0.6364	Remote Similarity	NPD8262	Approved
0.6344	Remote Similarity	NPD4697	Phase 3
0.6333	Remote Similarity	NPD7136	Phase 2
0.6322	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5285	Approved
0.6316	Remote Similarity	NPD4696	Approved
0.6316	Remote Similarity	NPD5286	Approved
0.631	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD6672	Approved
0.6292	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD6903	Approved
0.6292	Remote Similarity	NPD4722	Approved
0.6292	Remote Similarity	NPD5737	Approved
0.6292	Remote Similarity	NPD4723	Approved
0.6277	Remote Similarity	NPD4755	Approved
0.6277	Remote Similarity	NPD7902	Approved
0.6264	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD5223	Approved
0.6235	Remote Similarity	NPD4139	Approved
0.6235	Remote Similarity	NPD4692	Approved
0.6222	Remote Similarity	NPD6051	Approved
0.6211	Remote Similarity	NPD7638	Approved
0.6196	Remote Similarity	NPD5133	Approved
0.6186	Remote Similarity	NPD5224	Approved
0.6186	Remote Similarity	NPD5211	Phase 2
0.6186	Remote Similarity	NPD5225	Approved
0.6186	Remote Similarity	NPD5226	Approved
0.6186	Remote Similarity	NPD4633	Approved
0.6173	Remote Similarity	NPD5733	Approved
0.6173	Remote Similarity	NPD4687	Approved
0.6154	Remote Similarity	NPD4096	Approved
0.6154	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4700	Approved
0.6146	Remote Similarity	NPD7639	Approved
0.6146	Remote Similarity	NPD7640	Approved
0.6136	Remote Similarity	NPD1696	Phase 3
0.6122	Remote Similarity	NPD5174	Approved
0.6122	Remote Similarity	NPD5175	Approved
0.6111	Remote Similarity	NPD4518	Approved
0.6098	Remote Similarity	NPD8039	Approved
0.6076	Remote Similarity	NPD4137	Phase 3
0.6076	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6098	Approved
0.6064	Remote Similarity	NPD5695	Phase 3
0.6061	Remote Similarity	NPD5141	Approved
0.6053	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4732	Discontinued
0.6042	Remote Similarity	NPD5696	Approved
0.604	Remote Similarity	NPD6881	Approved
0.604	Remote Similarity	NPD6899	Approved
0.6022	Remote Similarity	NPD5779	Approved
0.6022	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD4194	Approved
0.6	Remote Similarity	NPD4787	Phase 1
0.6	Remote Similarity	NPD4244	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD4192	Approved
0.6	Remote Similarity	NPD4691	Approved
0.6	Remote Similarity	NPD4193	Approved
0.6	Remote Similarity	NPD4789	Approved
0.6	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD7614	Phase 1
0.6	Remote Similarity	NPD4747	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6939	Phase 2
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD4191	Approved
0.6	Remote Similarity	NPD4245	Approved
0.5979	Remote Similarity	NPD6404	Discontinued
0.5978	Remote Similarity	NPD5207	Approved
0.5978	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4754	Approved
0.5957	Remote Similarity	NPD7900	Approved
0.5957	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5771	Approved
0.5949	Remote Similarity	NPD6705	Phase 1
0.5941	Remote Similarity	NPD6412	Phase 2
0.5941	Remote Similarity	NPD5697	Approved
0.5938	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5276	Approved
0.5922	Remote Similarity	NPD7290	Approved
0.5922	Remote Similarity	NPD6883	Approved
0.5922	Remote Similarity	NPD7102	Approved
0.5914	Remote Similarity	NPD5694	Approved
0.5914	Remote Similarity	NPD6050	Approved
0.5882	Remote Similarity	NPD4730	Approved
0.5882	Remote Similarity	NPD7320	Approved
0.5882	Remote Similarity	NPD5168	Approved
0.5882	Remote Similarity	NPD6011	Approved
0.5882	Remote Similarity	NPD4729	Approved
0.5875	Remote Similarity	NPD3700	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