NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	273.14
Volume:	277.888
LogP:	0.936
LogD:	1.006
LogS:	-2.078
# Rotatable Bonds:	1
TPSA:	52.93
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.762
Synthetic Accessibility Score:	4.819
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:	-4.75
MDCK Permeability:	1.9585084373829886e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.842
Human Intestinal Absorption (HIA):	0.145
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	33.676055908203125%
Volume Distribution (VD):	2.459
Pgp-substrate:	68.90006256103516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.107
CYP1A2-substrate:	0.763
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.838
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.466
CYP2D6-inhibitor:	0.653
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.55

ADMET: Excretion

Clearance (CL):	12.078
Half-life (T1/2):	0.85

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.399
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.501
Carcinogencity:	0.855
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC147091

Natural Product ID:	NPC147091
*Common Name:**	TZTBAJFJEZRQCV-RLCCDNCMSA-N
IUPAC Name:	n.a.
Synonyms:	8-O-Demethylmaritidine
Standard InCHIKey:	TZTBAJFJEZRQCV-RLCCDNCMSA-N
Standard InCHI:	InChI=1S/C16H19NO3/c1-20-14-8-12-10(6-13(14)19)9-17-5-4-16(12)3-2-11(18)7-15(16)17/h2-3,6,8,11,15,18-19H,4-5,7,9H2,1H3/t11-,15+,16+/m1/s1
SMILES:	COc1cc2c(cc1O)CN1[C@@H]3[C@@]2(C=C[C@H](C3)O)CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087242
PubChem CID:	443683
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000100] Phenanthridines and derivatives

*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
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9485	Haplopappus deserticola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9144	Atriplex parvifolia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17432	Ligularia przewalskii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1412	Artemisia juncea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19776	Hesperocyparis arizonica	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11000	Eupatorium laevigatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11473	Viburnum lantana	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13181	Ferula persica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26299	Reticularia lycoperdon	Species	Reticulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19610	Stachys aegyptiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
Others	1

Activity Type	# Activity
Individual Protein	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	57400.0	nM	PMID[573645]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	91500.0	nM	PMID[573644]
NPT35	Others	n.a.		permeability	=	0.7	10'-6 cm/s	PMID[573645]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	61.5	ug.mL-1	PMID[573646]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	90.0	ug.mL-1	PMID[573646]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	90.0	ug.mL-1	PMID[573646]

☑ 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 NPC147091 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	252
0.1-0.2	1313
0.2-0.3	4712
0.3-0.4	12557
0.4-0.5	6861
0.5-0.6	12439
0.6-0.7	3591
0.7-0.8	676
0.8-0.85	170
0.85-0.9	104
0.9-0.95	18
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9408	High Similarity	NPC205167
0.9408	High Similarity	NPC249274
0.9396	High Similarity	NPC82285
0.9396	High Similarity	NPC133011
0.9281	High Similarity	NPC215829
0.9281	High Similarity	NPC97072
0.9262	High Similarity	NPC274026
0.9189	High Similarity	NPC321505
0.9189	High Similarity	NPC179825
0.9189	High Similarity	NPC191376
0.9128	High Similarity	NPC147390
0.9128	High Similarity	NPC246587
0.9128	High Similarity	NPC135538
0.9128	High Similarity	NPC428
0.9128	High Similarity	NPC24233
0.9128	High Similarity	NPC476571
0.9067	High Similarity	NPC477565
0.9067	High Similarity	NPC103379
0.9054	High Similarity	NPC185838
0.902	High Similarity	NPC78733
0.8938	High Similarity	NPC225597
0.8938	High Similarity	NPC470739
0.8938	High Similarity	NPC477640
0.8933	High Similarity	NPC476151
0.8931	High Similarity	NPC58766
0.8931	High Similarity	NPC290759
0.8931	High Similarity	NPC475686
0.8931	High Similarity	NPC266176
0.8931	High Similarity	NPC82533
0.8931	High Similarity	NPC158148
0.8926	High Similarity	NPC130926
0.8903	High Similarity	NPC475326
0.8896	High Similarity	NPC172765
0.8896	High Similarity	NPC2413
0.8896	High Similarity	NPC193949
0.8896	High Similarity	NPC295691
0.8896	High Similarity	NPC189266
0.8896	High Similarity	NPC54379
0.8896	High Similarity	NPC278799
0.8896	High Similarity	NPC39701
0.8896	High Similarity	NPC110416
0.8896	High Similarity	NPC5238
0.8896	High Similarity	NPC249797
0.8896	High Similarity	NPC207757
0.8896	High Similarity	NPC469817
0.8896	High Similarity	NPC127674
0.8896	High Similarity	NPC204828
0.8896	High Similarity	NPC184026
0.8896	High Similarity	NPC276588
0.8882	High Similarity	NPC220858
0.8882	High Similarity	NPC192768
0.8882	High Similarity	NPC88249
0.8882	High Similarity	NPC97221
0.8882	High Similarity	NPC151895
0.8875	High Similarity	NPC474475
0.8868	High Similarity	NPC210140
0.8868	High Similarity	NPC100566
0.8846	High Similarity	NPC59028
0.8846	High Similarity	NPC92191
0.8824	High Similarity	NPC76213
0.8824	High Similarity	NPC277669
0.882	High Similarity	NPC476331
0.8805	High Similarity	NPC124657
0.879	High Similarity	NPC18402
0.8767	High Similarity	NPC131204
0.8767	High Similarity	NPC301050
0.875	High Similarity	NPC190332
0.875	High Similarity	NPC181653
0.8742	High Similarity	NPC238530
0.8742	High Similarity	NPC232514
0.8742	High Similarity	NPC276944
0.8742	High Similarity	NPC134858
0.8726	High Similarity	NPC111485
0.8716	High Similarity	NPC314682
0.871	High Similarity	NPC2295
0.871	High Similarity	NPC477564
0.8696	High Similarity	NPC470324
0.8693	High Similarity	NPC60538
0.8693	High Similarity	NPC207824
0.8679	High Similarity	NPC320104
0.8679	High Similarity	NPC233650
0.8659	High Similarity	NPC474470
0.8658	High Similarity	NPC474915
0.8658	High Similarity	NPC188163
0.8658	High Similarity	NPC328750
0.8658	High Similarity	NPC213206
0.8645	High Similarity	NPC148898
0.8645	High Similarity	NPC37272
0.8642	High Similarity	NPC311991
0.8609	High Similarity	NPC294249
0.8599	High Similarity	NPC186063
0.8554	High Similarity	NPC244554
0.8553	High Similarity	NPC27410
0.8553	High Similarity	NPC166014
0.8545	High Similarity	NPC237044
0.8544	High Similarity	NPC148014
0.8544	High Similarity	NPC78359
0.8544	High Similarity	NPC315707
0.8544	High Similarity	NPC65490
0.8544	High Similarity	NPC40389
0.8526	High Similarity	NPC26601
0.8519	High Similarity	NPC150879
0.8506	High Similarity	NPC475959
0.8494	Intermediate Similarity	NPC474325
0.8485	Intermediate Similarity	NPC304675
0.8481	Intermediate Similarity	NPC37205
0.8481	Intermediate Similarity	NPC160931
0.8466	Intermediate Similarity	NPC164429
0.8457	Intermediate Similarity	NPC13916
0.8457	Intermediate Similarity	NPC264850
0.8443	Intermediate Similarity	NPC474745
0.8442	Intermediate Similarity	NPC476144
0.8442	Intermediate Similarity	NPC106295
0.8442	Intermediate Similarity	NPC210437
0.8442	Intermediate Similarity	NPC51957
0.8442	Intermediate Similarity	NPC16107
0.8438	Intermediate Similarity	NPC4304
0.8424	Intermediate Similarity	NPC2314
0.8421	Intermediate Similarity	NPC476567
0.8421	Intermediate Similarity	NPC128019
0.8421	Intermediate Similarity	NPC136860
0.8415	Intermediate Similarity	NPC75958
0.8405	Intermediate Similarity	NPC252960
0.8395	Intermediate Similarity	NPC24465
0.8395	Intermediate Similarity	NPC247972
0.8387	Intermediate Similarity	NPC7467
0.8383	Intermediate Similarity	NPC15919
0.8373	Intermediate Similarity	NPC187678
0.8365	Intermediate Similarity	NPC323443
0.8365	Intermediate Similarity	NPC180756
0.8356	Intermediate Similarity	NPC160193
0.8354	Intermediate Similarity	NPC83198
0.8354	Intermediate Similarity	NPC204908
0.8344	Intermediate Similarity	NPC476002
0.8344	Intermediate Similarity	NPC317272
0.8344	Intermediate Similarity	NPC42549
0.8344	Intermediate Similarity	NPC256012
0.8344	Intermediate Similarity	NPC250846
0.8344	Intermediate Similarity	NPC268503
0.8344	Intermediate Similarity	NPC240841
0.8333	Intermediate Similarity	NPC193528
0.8333	Intermediate Similarity	NPC324144
0.8333	Intermediate Similarity	NPC218614
0.8333	Intermediate Similarity	NPC219162
0.8323	Intermediate Similarity	NPC226428
0.8313	Intermediate Similarity	NPC129603
0.8302	Intermediate Similarity	NPC216459
0.8302	Intermediate Similarity	NPC138487
0.8302	Intermediate Similarity	NPC41178
0.8294	Intermediate Similarity	NPC474746
0.8294	Intermediate Similarity	NPC475981
0.8293	Intermediate Similarity	NPC306555
0.8293	Intermediate Similarity	NPC145832
0.8293	Intermediate Similarity	NPC117188
0.8293	Intermediate Similarity	NPC205421
0.8293	Intermediate Similarity	NPC12053
0.8293	Intermediate Similarity	NPC298979
0.8293	Intermediate Similarity	NPC81218
0.8293	Intermediate Similarity	NPC474931
0.8293	Intermediate Similarity	NPC158376
0.8291	Intermediate Similarity	NPC223124
0.8282	Intermediate Similarity	NPC255607
0.8282	Intermediate Similarity	NPC96603
0.8282	Intermediate Similarity	NPC78222
0.8282	Intermediate Similarity	NPC284183
0.8282	Intermediate Similarity	NPC477563
0.8282	Intermediate Similarity	NPC136508
0.8282	Intermediate Similarity	NPC3375
0.8282	Intermediate Similarity	NPC13504
0.8282	Intermediate Similarity	NPC196447
0.8282	Intermediate Similarity	NPC4138
0.8282	Intermediate Similarity	NPC253043
0.8282	Intermediate Similarity	NPC121275
0.8282	Intermediate Similarity	NPC212794
0.8282	Intermediate Similarity	NPC306843
0.8282	Intermediate Similarity	NPC76116
0.8274	Intermediate Similarity	NPC21885
0.8272	Intermediate Similarity	NPC60186
0.8263	Intermediate Similarity	NPC49353
0.8261	Intermediate Similarity	NPC118804
0.825	Intermediate Similarity	NPC146288
0.8232	Intermediate Similarity	NPC81247
0.8232	Intermediate Similarity	NPC476573
0.8232	Intermediate Similarity	NPC35627
0.8225	Intermediate Similarity	NPC32154
0.8221	Intermediate Similarity	NPC124433
0.8221	Intermediate Similarity	NPC1229
0.8221	Intermediate Similarity	NPC293871
0.8212	Intermediate Similarity	NPC253429
0.8205	Intermediate Similarity	NPC95075
0.8205	Intermediate Similarity	NPC253883
0.8205	Intermediate Similarity	NPC90844
0.8204	Intermediate Similarity	NPC152680
0.8204	Intermediate Similarity	NPC232386
0.8204	Intermediate Similarity	NPC190783
0.8198	Intermediate Similarity	NPC230098
0.8182	Intermediate Similarity	NPC474324
0.8182	Intermediate Similarity	NPC57812
0.8176	Intermediate Similarity	NPC233029
0.8176	Intermediate Similarity	NPC210148

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 NPC147091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	652
0.2-0.3	882
0.3-0.4	2108
0.4-0.5	2721
0.5-0.6	1748
0.6-0.7	689
0.7-0.8	159
0.8-0.85	13
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD4772	Phase 2
0.871	High Similarity	NPD4773	Phase 2
0.8696	High Similarity	NPD2489	Approved
0.8696	High Similarity	NPD2898	Approved
0.8696	High Similarity	NPD27	Approved
0.8658	High Similarity	NPD4664	Clinical (unspecified phase)
0.8571	High Similarity	NPD6071	Discontinued
0.8544	High Similarity	NPD2563	Approved
0.8544	High Similarity	NPD2560	Approved
0.8519	High Similarity	NPD2970	Approved
0.8519	High Similarity	NPD2969	Approved
0.8442	Intermediate Similarity	NPD4584	Approved
0.8366	Intermediate Similarity	NPD5241	Discontinued
0.8344	Intermediate Similarity	NPD3051	Approved
0.8232	Intermediate Similarity	NPD4010	Discontinued
0.821	Intermediate Similarity	NPD7831	Phase 2
0.821	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD7833	Phase 2
0.8205	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD4017	Approved
0.8101	Intermediate Similarity	NPD3639	Approved
0.8101	Intermediate Similarity	NPD3640	Phase 3
0.8101	Intermediate Similarity	NPD3641	Approved
0.807	Intermediate Similarity	NPD7312	Approved
0.807	Intermediate Similarity	NPD7313	Approved
0.807	Intermediate Similarity	NPD7310	Approved
0.807	Intermediate Similarity	NPD7311	Approved
0.8023	Intermediate Similarity	NPD7309	Approved
0.8	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7906	Approved
0.7987	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD4577	Approved
0.7965	Intermediate Similarity	NPD4578	Approved
0.7931	Intermediate Similarity	NPD4663	Approved
0.7919	Intermediate Similarity	NPD8053	Approved
0.7919	Intermediate Similarity	NPD8054	Approved
0.7885	Intermediate Similarity	NPD4236	Phase 3
0.7885	Intermediate Similarity	NPD4237	Approved
0.7881	Intermediate Similarity	NPD2674	Phase 3
0.7875	Intermediate Similarity	NPD6031	Approved
0.7875	Intermediate Similarity	NPD6030	Approved
0.7853	Intermediate Similarity	NPD7298	Approved
0.7844	Intermediate Similarity	NPD6107	Approved
0.7811	Intermediate Similarity	NPD4481	Phase 3
0.7805	Intermediate Similarity	NPD5772	Approved
0.7805	Intermediate Similarity	NPD2978	Approved
0.7805	Intermediate Similarity	NPD5773	Approved
0.7805	Intermediate Similarity	NPD2977	Approved
0.7799	Intermediate Similarity	NPD2421	Approved
0.7799	Intermediate Similarity	NPD2420	Approved
0.7798	Intermediate Similarity	NPD4166	Phase 2
0.7797	Intermediate Similarity	NPD2490	Approved
0.7797	Intermediate Similarity	NPD2488	Approved
0.7771	Intermediate Similarity	NPD5177	Phase 3
0.7736	Intermediate Similarity	NPD3845	Phase 1
0.7697	Intermediate Similarity	NPD3145	Approved
0.7697	Intermediate Similarity	NPD5718	Phase 2
0.7697	Intermediate Similarity	NPD3144	Approved
0.7658	Intermediate Similarity	NPD3060	Approved
0.7657	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1753	Discontinued
0.7628	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3124	Discontinued
0.7572	Intermediate Similarity	NPD5313	Approved
0.7572	Intermediate Similarity	NPD8156	Discontinued
0.7572	Intermediate Similarity	NPD5312	Approved
0.7566	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6895	Approved
0.7564	Intermediate Similarity	NPD6896	Approved
0.7562	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4162	Approved
0.7514	Intermediate Similarity	NPD8099	Discontinued
0.7514	Intermediate Similarity	NPD8252	Approved
0.7514	Intermediate Similarity	NPD8251	Approved
0.75	Intermediate Similarity	NPD823	Approved
0.75	Intermediate Similarity	NPD817	Approved
0.75	Intermediate Similarity	NPD6788	Approved
0.7486	Intermediate Similarity	NPD6297	Approved
0.7484	Intermediate Similarity	NPD3109	Approved
0.7484	Intermediate Similarity	NPD3110	Approved
0.7484	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2238	Phase 2
0.7484	Intermediate Similarity	NPD3620	Phase 2
0.7457	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2494	Approved
0.7419	Intermediate Similarity	NPD3450	Approved
0.7419	Intermediate Similarity	NPD2493	Approved
0.7419	Intermediate Similarity	NPD3452	Approved
0.7416	Intermediate Similarity	NPD6851	Approved
0.7416	Intermediate Similarity	NPD6853	Approved
0.7403	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3637	Approved
0.7386	Intermediate Similarity	NPD3636	Approved
0.7386	Intermediate Similarity	NPD3635	Approved
0.738	Intermediate Similarity	NPD3448	Approved
0.738	Intermediate Similarity	NPD2491	Approved
0.736	Intermediate Similarity	NPD7281	Phase 3
0.736	Intermediate Similarity	NPD2971	Approved
0.736	Intermediate Similarity	NPD7280	Phase 3
0.736	Intermediate Similarity	NPD2968	Approved
0.7358	Intermediate Similarity	NPD2161	Phase 2
0.7349	Intermediate Similarity	NPD824	Approved
0.7346	Intermediate Similarity	NPD3692	Discontinued
0.7341	Intermediate Similarity	NPD6688	Approved
0.7341	Intermediate Similarity	NPD6687	Approved
0.7337	Intermediate Similarity	NPD5977	Approved
0.7337	Intermediate Similarity	NPD5978	Approved
0.7326	Intermediate Similarity	NPD7802	Discontinued
0.7317	Intermediate Similarity	NPD3645	Discontinued
0.7317	Intermediate Similarity	NPD1424	Approved
0.7315	Intermediate Similarity	NPD2668	Approved
0.7315	Intermediate Similarity	NPD2667	Approved
0.7308	Intermediate Similarity	NPD4474	Approved
0.7308	Intermediate Similarity	NPD1132	Approved
0.7308	Intermediate Similarity	NPD4475	Approved
0.7308	Intermediate Similarity	NPD1136	Approved
0.7308	Intermediate Similarity	NPD1130	Approved
0.7308	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4040	Phase 1
0.7302	Intermediate Similarity	NPD4583	Approved
0.7302	Intermediate Similarity	NPD4582	Approved
0.7294	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4210	Discontinued
0.7287	Intermediate Similarity	NPD3057	Approved
0.7285	Intermediate Similarity	NPD2230	Approved
0.7285	Intermediate Similarity	NPD2232	Approved
0.7285	Intermediate Similarity	NPD2233	Approved
0.7284	Intermediate Similarity	NPD6331	Phase 2
0.7273	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD52	Approved
0.7273	Intermediate Similarity	NPD7526	Approved
0.7267	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7037	Approved
0.7255	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3055	Approved
0.7255	Intermediate Similarity	NPD3053	Approved
0.7255	Intermediate Similarity	NPD4103	Phase 2
0.7249	Intermediate Similarity	NPD4004	Approved
0.7249	Intermediate Similarity	NPD4002	Approved
0.7246	Intermediate Similarity	NPD4005	Discontinued
0.7246	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD601	Approved
0.7244	Intermediate Similarity	NPD598	Approved
0.7244	Intermediate Similarity	NPD597	Approved
0.7239	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5160	Discontinued
0.7226	Intermediate Similarity	NPD2606	Approved
0.7226	Intermediate Similarity	NPD3594	Approved
0.7226	Intermediate Similarity	NPD2605	Approved
0.7226	Intermediate Similarity	NPD3595	Approved
0.7205	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3656	Approved
0.7204	Intermediate Similarity	NPD2974	Approved
0.7204	Intermediate Similarity	NPD2975	Approved
0.7204	Intermediate Similarity	NPD2973	Approved
0.7196	Intermediate Similarity	NPD2972	Approved
0.7196	Intermediate Similarity	NPD3533	Approved
0.7195	Intermediate Similarity	NPD7124	Phase 2
0.7179	Intermediate Similarity	NPD5156	Approved
0.7179	Intermediate Similarity	NPD5155	Approved
0.7178	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4873	Discontinued
0.7169	Intermediate Similarity	NPD6090	Discontinued
0.7168	Intermediate Similarity	NPD2904	Discontinued
0.716	Intermediate Similarity	NPD7153	Discontinued
0.716	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5582	Discontinued
0.7151	Intermediate Similarity	NPD5604	Discontinued
0.7151	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2122	Discontinued
0.7124	Intermediate Similarity	NPD4659	Approved
0.712	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5720	Discontinued
0.7108	Intermediate Similarity	NPD2874	Phase 2
0.7108	Intermediate Similarity	NPD7020	Approved
0.7108	Intermediate Similarity	NPD7019	Approved
0.7108	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4123	Phase 3
0.7097	Intermediate Similarity	NPD7905	Discontinued
0.709	Intermediate Similarity	NPD4580	Approved
0.7086	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3686	Approved
0.7083	Intermediate Similarity	NPD3687	Approved
0.7081	Intermediate Similarity	NPD2154	Approved
0.7081	Intermediate Similarity	NPD2156	Approved
0.7081	Intermediate Similarity	NPD2155	Approved
0.7078	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4420	Approved
0.7073	Intermediate Similarity	NPD6748	Discontinued
0.7073	Intermediate Similarity	NPD5754	Discontinued

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