NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	273.14
Volume:	277.888
LogP:	1.053
LogD:	0.508
LogS:	-1.655
# Rotatable Bonds:	0
TPSA:	52.93
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.704
Synthetic Accessibility Score:	4.347
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.168
MDCK Permeability:	1.1964937584707513e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.879
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.999
Plasma Protein Binding (PPB):	19.432174682617188%
Volume Distribution (VD):	2.533
Pgp-substrate:	79.83293914794922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.197
CYP1A2-substrate:	0.545
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.536
CYP2D6-inhibitor:	0.784
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.612

ADMET: Excretion

Clearance (CL):	5.907
Half-life (T1/2):	0.615

ADMET: Toxicity

hERG Blockers:	0.419
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.147
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.758
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.842
Carcinogencity:	0.137
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC18402

Natural Product ID:	NPC18402
*Common Name:**	Sanguinine
IUPAC Name:	n.a.
Synonyms:	Sanguinine
Standard InCHIKey:	OYSGWKOGUVOGFQ-RBOXIYTFSA-N
Standard InCHI:	InChI=1S/C16H19NO3/c1-17-7-6-16-5-4-11(18)8-13(16)20-15-12(19)3-2-10(9-17)14(15)16/h2-5,11,13,18-19H,6-9H2,1H3/t11-,13-,16-/m0/s1
SMILES:	O[C@H]1C=C[C@@]23[C@H](C1)Oc1c3c(ccc1O)CN(CC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1524
PubChem CID:	443722
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004128] Galanthamine-type amaryllidaceae alkaloids

*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
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	whole plants	n.a.	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2348199]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26913788]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26604	Aralia subcapitata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO272	Pittosporum eugenioides	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26604	Aralia subcapitata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26154	Erythropodium caribaeorum	Species	Anthothelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26641	Pteroxygonum giraldii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13480	Stereocaulon dactylophyllum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	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	4

Activity Type	# Activity
Individual Protein	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	100.0	nM	PMID[477009]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	22.5	ug.mL-1	PMID[477010]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	30.0	ug.mL-1	PMID[477010]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	30.0	ug.mL-1	PMID[477010]

☑ 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 NPC18402 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	260
0.1-0.2	1325
0.2-0.3	4941
0.3-0.4	12723
0.4-0.5	5242
0.5-0.6	10946
0.6-0.7	5737
0.7-0.8	1297
0.8-0.85	190
0.85-0.9	20
0.9-0.95	9
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC65490
0.9733	High Similarity	NPC40389
0.9733	High Similarity	NPC148014
0.9733	High Similarity	NPC315707
0.9733	High Similarity	NPC78359
0.9474	High Similarity	NPC129603
0.9355	High Similarity	NPC293871
0.9355	High Similarity	NPC124433
0.879	High Similarity	NPC147091
0.8758	High Similarity	NPC124657
0.8589	High Similarity	NPC284842
0.8537	High Similarity	NPC83198
0.8537	High Similarity	NPC204908
0.8509	High Similarity	NPC205167
0.8509	High Similarity	NPC249274
0.8481	Intermediate Similarity	NPC82285
0.8481	Intermediate Similarity	NPC133011
0.8408	Intermediate Similarity	NPC103379
0.8408	Intermediate Similarity	NPC477565
0.8383	Intermediate Similarity	NPC232386
0.8383	Intermediate Similarity	NPC152680
0.8383	Intermediate Similarity	NPC190783
0.8354	Intermediate Similarity	NPC274026
0.8344	Intermediate Similarity	NPC131204
0.8344	Intermediate Similarity	NPC301050
0.8323	Intermediate Similarity	NPC323443
0.8323	Intermediate Similarity	NPC180756
0.8303	Intermediate Similarity	NPC476002
0.828	Intermediate Similarity	NPC179825
0.828	Intermediate Similarity	NPC321505
0.828	Intermediate Similarity	NPC476151
0.828	Intermediate Similarity	NPC191376
0.8228	Intermediate Similarity	NPC428
0.8228	Intermediate Similarity	NPC24233
0.8228	Intermediate Similarity	NPC147390
0.8228	Intermediate Similarity	NPC476571
0.8228	Intermediate Similarity	NPC135538
0.8228	Intermediate Similarity	NPC246587
0.8221	Intermediate Similarity	NPC92191
0.8221	Intermediate Similarity	NPC59028
0.8214	Intermediate Similarity	NPC476331
0.8199	Intermediate Similarity	NPC475557
0.8171	Intermediate Similarity	NPC215829
0.8171	Intermediate Similarity	NPC97072
0.8153	Intermediate Similarity	NPC185838
0.8148	Intermediate Similarity	NPC204828
0.8148	Intermediate Similarity	NPC5238
0.8148	Intermediate Similarity	NPC249797
0.8148	Intermediate Similarity	NPC110416
0.8148	Intermediate Similarity	NPC469817
0.8148	Intermediate Similarity	NPC295691
0.8148	Intermediate Similarity	NPC193949
0.8148	Intermediate Similarity	NPC189266
0.8148	Intermediate Similarity	NPC39701
0.8148	Intermediate Similarity	NPC127674
0.8148	Intermediate Similarity	NPC172765
0.8148	Intermediate Similarity	NPC54379
0.8148	Intermediate Similarity	NPC207757
0.8148	Intermediate Similarity	NPC278799
0.8148	Intermediate Similarity	NPC2413
0.8148	Intermediate Similarity	NPC184026
0.8148	Intermediate Similarity	NPC276588
0.814	Intermediate Similarity	NPC305847
0.8121	Intermediate Similarity	NPC60186
0.8118	Intermediate Similarity	NPC49353
0.8107	Intermediate Similarity	NPC470739
0.8107	Intermediate Similarity	NPC225597
0.8107	Intermediate Similarity	NPC477640
0.8098	Intermediate Similarity	NPC160931
0.8098	Intermediate Similarity	NPC37205
0.8095	Intermediate Similarity	NPC58766
0.8095	Intermediate Similarity	NPC470324
0.8095	Intermediate Similarity	NPC266176
0.8095	Intermediate Similarity	NPC290759
0.8095	Intermediate Similarity	NPC475686
0.8095	Intermediate Similarity	NPC82533
0.8095	Intermediate Similarity	NPC158148
0.8092	Intermediate Similarity	NPC302449
0.8086	Intermediate Similarity	NPC477564
0.8086	Intermediate Similarity	NPC2295
0.8084	Intermediate Similarity	NPC13916
0.8084	Intermediate Similarity	NPC264850
0.8081	Intermediate Similarity	NPC244554
0.8049	Intermediate Similarity	NPC475326
0.8047	Intermediate Similarity	NPC474475
0.8038	Intermediate Similarity	NPC130926
0.8036	Intermediate Similarity	NPC210140
0.8036	Intermediate Similarity	NPC100566
0.8024	Intermediate Similarity	NPC276944
0.8024	Intermediate Similarity	NPC232514
0.8024	Intermediate Similarity	NPC238530
0.8024	Intermediate Similarity	NPC24465
0.8012	Intermediate Similarity	NPC151895
0.8012	Intermediate Similarity	NPC192768
0.8012	Intermediate Similarity	NPC220858
0.8012	Intermediate Similarity	NPC97221
0.8012	Intermediate Similarity	NPC88249
0.7977	Intermediate Similarity	NPC99179
0.7966	Intermediate Similarity	NPC206900
0.7965	Intermediate Similarity	NPC474470
0.7964	Intermediate Similarity	NPC324144
0.7963	Intermediate Similarity	NPC76213
0.7963	Intermediate Similarity	NPC277669
0.7953	Intermediate Similarity	NPC2314
0.7952	Intermediate Similarity	NPC27410
0.7952	Intermediate Similarity	NPC166014
0.7947	Intermediate Similarity	NPC160193
0.7941	Intermediate Similarity	NPC75958
0.7941	Intermediate Similarity	NPC311991
0.7931	Intermediate Similarity	NPC286119
0.7929	Intermediate Similarity	NPC306555
0.7929	Intermediate Similarity	NPC474931
0.7929	Intermediate Similarity	NPC81218
0.7929	Intermediate Similarity	NPC117188
0.7929	Intermediate Similarity	NPC150879
0.7929	Intermediate Similarity	NPC205421
0.7929	Intermediate Similarity	NPC12053
0.7929	Intermediate Similarity	NPC145832
0.7929	Intermediate Similarity	NPC181653
0.7929	Intermediate Similarity	NPC190332
0.7929	Intermediate Similarity	NPC158376
0.7927	Intermediate Similarity	NPC78733
0.7919	Intermediate Similarity	NPC15919
0.7917	Intermediate Similarity	NPC212794
0.7917	Intermediate Similarity	NPC306843
0.7917	Intermediate Similarity	NPC96603
0.7917	Intermediate Similarity	NPC13504
0.7917	Intermediate Similarity	NPC196447
0.7917	Intermediate Similarity	NPC253043
0.7917	Intermediate Similarity	NPC78222
0.7917	Intermediate Similarity	NPC136508
0.7917	Intermediate Similarity	NPC134858
0.7917	Intermediate Similarity	NPC477563
0.7907	Intermediate Similarity	NPC187678
0.7892	Intermediate Similarity	NPC111485
0.7886	Intermediate Similarity	NPC181796
0.7886	Intermediate Similarity	NPC49075
0.7886	Intermediate Similarity	NPC90998
0.7886	Intermediate Similarity	NPC251735
0.7886	Intermediate Similarity	NPC54654
0.7886	Intermediate Similarity	NPC7715
0.7886	Intermediate Similarity	NPC182052
0.7886	Intermediate Similarity	NPC8836
0.7886	Intermediate Similarity	NPC290005
0.7886	Intermediate Similarity	NPC42663
0.7886	Intermediate Similarity	NPC239824
0.7886	Intermediate Similarity	NPC223690
0.7886	Intermediate Similarity	NPC279228
0.7886	Intermediate Similarity	NPC285931
0.7886	Intermediate Similarity	NPC217748
0.7886	Intermediate Similarity	NPC311973
0.7886	Intermediate Similarity	NPC104196
0.7886	Intermediate Similarity	NPC30779
0.7886	Intermediate Similarity	NPC185639
0.7886	Intermediate Similarity	NPC229373
0.7886	Intermediate Similarity	NPC258657
0.7886	Intermediate Similarity	NPC328155
0.7886	Intermediate Similarity	NPC271013
0.7886	Intermediate Similarity	NPC15414
0.7886	Intermediate Similarity	NPC222661
0.7886	Intermediate Similarity	NPC290582
0.7882	Intermediate Similarity	NPC164429
0.7874	Intermediate Similarity	NPC32154
0.787	Intermediate Similarity	NPC42549
0.787	Intermediate Similarity	NPC268503
0.787	Intermediate Similarity	NPC256012
0.787	Intermediate Similarity	NPC240841
0.787	Intermediate Similarity	NPC250846
0.787	Intermediate Similarity	NPC317272
0.7862	Intermediate Similarity	NPC294249
0.7861	Intermediate Similarity	NPC237044
0.7857	Intermediate Similarity	NPC320104
0.7857	Intermediate Similarity	NPC233650
0.7857	Intermediate Similarity	NPC1229
0.7844	Intermediate Similarity	NPC4304
0.7844	Intermediate Similarity	NPC165797
0.7841	Intermediate Similarity	NPC167116
0.7841	Intermediate Similarity	NPC274716
0.7841	Intermediate Similarity	NPC254441
0.784	Intermediate Similarity	NPC60538
0.784	Intermediate Similarity	NPC207824
0.7836	Intermediate Similarity	NPC118274
0.7836	Intermediate Similarity	NPC168753
0.7836	Intermediate Similarity	NPC329911
0.7834	Intermediate Similarity	NPC314682
0.7824	Intermediate Similarity	NPC252960
0.7816	Intermediate Similarity	NPC114364
0.7816	Intermediate Similarity	NPC320223
0.7816	Intermediate Similarity	NPC474325
0.7815	Intermediate Similarity	NPC172403
0.7805	Intermediate Similarity	NPC37272
0.7805	Intermediate Similarity	NPC148898
0.7803	Intermediate Similarity	NPC199465
0.7803	Intermediate Similarity	NPC304675
0.7803	Intermediate Similarity	NPC128560
0.7803	Intermediate Similarity	NPC329969
0.7803	Intermediate Similarity	NPC229166
0.7797	Intermediate Similarity	NPC9867
0.7791	Intermediate Similarity	NPC239775
0.7785	Intermediate Similarity	NPC328750

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 NPC18402 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	716
0.2-0.3	1054
0.3-0.4	2358
0.4-0.5	2398
0.5-0.6	1550
0.6-0.7	693
0.7-0.8	180
0.8-0.85	13
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9733	High Similarity	NPD2563	Approved
0.9733	High Similarity	NPD2560	Approved
0.9359	High Similarity	NPD6071	Discontinued
0.865	High Similarity	NPD2489	Approved
0.865	High Similarity	NPD27	Approved
0.8476	Intermediate Similarity	NPD2970	Approved
0.8476	Intermediate Similarity	NPD2969	Approved
0.8303	Intermediate Similarity	NPD3051	Approved
0.8282	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD7831	Phase 2
0.8282	Intermediate Similarity	NPD7833	Phase 2
0.814	Intermediate Similarity	NPD7313	Approved
0.814	Intermediate Similarity	NPD7311	Approved
0.814	Intermediate Similarity	NPD7312	Approved
0.814	Intermediate Similarity	NPD7310	Approved
0.8095	Intermediate Similarity	NPD2898	Approved
0.8092	Intermediate Similarity	NPD7309	Approved
0.8086	Intermediate Similarity	NPD4772	Phase 2
0.8086	Intermediate Similarity	NPD4773	Phase 2
0.8057	Intermediate Similarity	NPD7906	Approved
0.8035	Intermediate Similarity	NPD4578	Approved
0.8035	Intermediate Similarity	NPD4577	Approved
0.8	Intermediate Similarity	NPD4663	Approved
0.7937	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD8054	Approved
0.7886	Intermediate Similarity	NPD8053	Approved
0.7785	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4481	Phase 3
0.7765	Intermediate Similarity	NPD2490	Approved
0.7765	Intermediate Similarity	NPD2488	Approved
0.7763	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD5241	Discontinued
0.7736	Intermediate Similarity	NPD3060	Approved
0.7727	Intermediate Similarity	NPD2674	Phase 3
0.7716	Intermediate Similarity	NPD4584	Approved
0.7707	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2238	Phase 2
0.7665	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4162	Approved
0.7625	Intermediate Similarity	NPD5177	Phase 3
0.7625	Intermediate Similarity	NPD4237	Approved
0.7625	Intermediate Similarity	NPD4236	Phase 3
0.7622	Intermediate Similarity	NPD6030	Approved
0.7622	Intermediate Similarity	NPD6031	Approved
0.7574	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5772	Approved
0.756	Intermediate Similarity	NPD5773	Approved
0.756	Intermediate Similarity	NPD2977	Approved
0.756	Intermediate Similarity	NPD2978	Approved
0.7548	Intermediate Similarity	NPD3145	Approved
0.7548	Intermediate Similarity	NPD3144	Approved
0.7547	Intermediate Similarity	NPD2161	Phase 2
0.7544	Intermediate Similarity	NPD3365	Discontinued
0.7543	Intermediate Similarity	NPD8156	Discontinued
0.7515	Intermediate Similarity	NPD5976	Discontinued
0.75	Intermediate Similarity	NPD4123	Phase 3
0.7487	Intermediate Similarity	NPD2493	Approved
0.7487	Intermediate Similarity	NPD2494	Approved
0.7487	Intermediate Similarity	NPD3452	Approved
0.7487	Intermediate Similarity	NPD3450	Approved
0.7486	Intermediate Similarity	NPD8251	Approved
0.7486	Intermediate Similarity	NPD8252	Approved
0.7486	Intermediate Similarity	NPD8099	Discontinued
0.7484	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3687	Approved
0.747	Intermediate Similarity	NPD3686	Approved
0.747	Intermediate Similarity	NPD4210	Discontinued
0.7457	Intermediate Similarity	NPD4010	Discontinued
0.7455	Intermediate Similarity	NPD6090	Discontinued
0.7423	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2677	Approved
0.7423	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6895	Approved
0.7421	Intermediate Similarity	NPD6896	Approved
0.7394	Intermediate Similarity	NPD1424	Approved
0.7391	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4678	Approved
0.7381	Intermediate Similarity	NPD4675	Approved
0.7378	Intermediate Similarity	NPD7124	Phase 2
0.7368	Intermediate Similarity	NPD4582	Approved
0.7368	Intermediate Similarity	NPD4583	Approved
0.7362	Intermediate Similarity	NPD6331	Phase 2
0.7354	Intermediate Similarity	NPD3448	Approved
0.7354	Intermediate Similarity	NPD2491	Approved
0.7346	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7153	Discontinued
0.7345	Intermediate Similarity	NPD4873	Discontinued
0.7341	Intermediate Similarity	NPD4666	Phase 3
0.7337	Intermediate Similarity	NPD6072	Discontinued
0.7333	Intermediate Similarity	NPD2971	Approved
0.7333	Intermediate Similarity	NPD2968	Approved
0.7325	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4017	Approved
0.7321	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3692	Discontinued
0.7316	Intermediate Similarity	NPD4002	Approved
0.7316	Intermediate Similarity	NPD4004	Approved
0.7305	Intermediate Similarity	NPD3640	Phase 3
0.7305	Intermediate Similarity	NPD3641	Approved
0.7305	Intermediate Similarity	NPD3639	Approved
0.7294	Intermediate Similarity	NPD5720	Discontinued
0.7289	Intermediate Similarity	NPD7020	Approved
0.7289	Intermediate Similarity	NPD7019	Approved
0.7289	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1375	Discontinued
0.7283	Intermediate Similarity	NPD5709	Phase 3
0.7278	Intermediate Similarity	NPD4474	Approved
0.7278	Intermediate Similarity	NPD4475	Approved
0.7273	Intermediate Similarity	NPD2974	Approved
0.7273	Intermediate Similarity	NPD2973	Approved
0.7273	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2975	Approved
0.7273	Intermediate Similarity	NPD6667	Approved
0.7273	Intermediate Similarity	NPD6666	Approved
0.7267	Intermediate Similarity	NPD6788	Approved
0.7263	Intermediate Similarity	NPD3057	Approved
0.7241	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7037	Approved
0.7233	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3620	Phase 2
0.7229	Intermediate Similarity	NPD2421	Approved
0.7229	Intermediate Similarity	NPD2420	Approved
0.7225	Intermediate Similarity	NPD4055	Discovery
0.7222	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3443	Approved
0.7219	Intermediate Similarity	NPD3444	Approved
0.7219	Intermediate Similarity	NPD3445	Approved
0.7219	Intermediate Similarity	NPD824	Approved
0.7215	Intermediate Similarity	NPD5718	Phase 2
0.7212	Intermediate Similarity	NPD5160	Discontinued
0.7205	Intermediate Similarity	NPD6111	Discontinued
0.7188	Intermediate Similarity	NPD4040	Phase 1
0.7174	Intermediate Similarity	NPD3398	Discontinued
0.7173	Intermediate Similarity	NPD2972	Approved
0.7173	Intermediate Similarity	NPD3533	Approved
0.716	Intermediate Similarity	NPD2156	Approved
0.716	Intermediate Similarity	NPD2154	Approved
0.716	Intermediate Similarity	NPD2155	Approved
0.7158	Intermediate Similarity	NPD4580	Approved
0.7152	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3027	Phase 3
0.7151	Intermediate Similarity	NPD7296	Approved
0.7143	Intermediate Similarity	NPD3054	Approved
0.7143	Intermediate Similarity	NPD3052	Approved
0.7143	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2232	Approved
0.7143	Intermediate Similarity	NPD7526	Approved
0.7143	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2233	Approved
0.7143	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2157	Approved
0.7143	Intermediate Similarity	NPD2230	Approved
0.7143	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD52	Approved
0.7134	Intermediate Similarity	NPD2170	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1712	Approved
0.7128	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3059	Approved
0.7125	Intermediate Similarity	NPD1613	Approved
0.7125	Intermediate Similarity	NPD3062	Approved
0.7125	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3061	Approved
0.7114	Intermediate Similarity	NPD1791	Approved
0.7114	Intermediate Similarity	NPD1793	Approved
0.7107	Intermediate Similarity	NPD601	Approved
0.7107	Intermediate Similarity	NPD598	Approved
0.7107	Intermediate Similarity	NPD597	Approved
0.7104	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6107	Approved
0.7101	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7298	Approved
0.7085	Intermediate Similarity	NPD7047	Phase 3
0.7073	Intermediate Similarity	NPD3656	Approved
0.707	Intermediate Similarity	NPD6584	Phase 3
0.707	Intermediate Similarity	NPD9621	Approved
0.707	Intermediate Similarity	NPD9620	Approved
0.707	Intermediate Similarity	NPD9619	Approved
0.7063	Intermediate Similarity	NPD1136	Approved
0.7063	Intermediate Similarity	NPD1130	Approved
0.7063	Intermediate Similarity	NPD1132	Approved
0.7059	Intermediate Similarity	NPD2667	Approved
0.7059	Intermediate Similarity	NPD1751	Approved
0.7059	Intermediate Similarity	NPD2668	Approved
0.7056	Intermediate Similarity	NPD6042	Phase 2
0.7056	Intermediate Similarity	NPD42	Phase 2
0.7055	Intermediate Similarity	NPD1753	Discontinued
0.7048	Intermediate Similarity	NPD6748	Discontinued
0.7044	Intermediate Similarity	NPD6997	Phase 2
0.7041	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD817	Approved
0.7037	Intermediate Similarity	NPD823	Approved
0.7037	Intermediate Similarity	NPD5314	Approved
0.7033	Intermediate Similarity	NPD3303	Discontinued
0.7024	Intermediate Similarity	NPD7213	Phase 3
0.7024	Intermediate Similarity	NPD1774	Approved
0.7024	Intermediate Similarity	NPD7212	Phase 2
0.7022	Intermediate Similarity	NPD6688	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