NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	273.14
Volume:	277.888
LogP:	1.08
LogD:	0.819
LogS:	-1.076
# Rotatable Bonds:	1
TPSA:	50.72
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.762
Synthetic Accessibility Score:	4.37
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.695
MDCK Permeability:	1.114902534027351e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.307
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974
Plasma Protein Binding (PPB):	11.295099258422852%
Volume Distribution (VD):	2.976
Pgp-substrate:	79.23280334472656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.359
CYP1A2-substrate:	0.504
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.324
CYP2D6-inhibitor:	0.654
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.249
CYP3A4-substrate:	0.431

ADMET: Excretion

Clearance (CL):	5.214
Half-life (T1/2):	0.522

ADMET: Toxicity

hERG Blockers:	0.46
Human Hepatotoxicity (H-HT):	0.541
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.881
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.783
Carcinogencity:	0.576
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC124433

Natural Product ID:	NPC124433
*Common Name:**	AIXQQSTVOSFSMO-FFSVYQOJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AIXQQSTVOSFSMO-FFSVYQOJSA-N
Standard InCHI:	InChI=1S/C16H19NO3/c1-19-12-3-2-10-9-17-7-6-16-5-4-11(18)8-13(16)20-15(12)14(10)16/h2-5,11,13,17-18H,6-9H2,1H3/t11-,13+,16+/m1/s1
SMILES:	COc1ccc2c3c1O[C@@H]1[C@@]3(CCNC2)C=C[C@H](C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3604339
PubChem CID:	443721
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
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]
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]
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]
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]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2668	Individual Protein	Acetylcholinesterase	Torpedo californica	IC50	=	15000.0	nM	PMID[553285]

☑ 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 NPC124433 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	251
0.1-0.2	1313
0.2-0.3	5071
0.3-0.4	12539
0.4-0.5	5499
0.5-0.6	12301
0.6-0.7	4741
0.7-0.8	880
0.8-0.85	85
0.85-0.9	2
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC293871
0.9605	High Similarity	NPC315707
0.9605	High Similarity	NPC78359
0.9605	High Similarity	NPC40389
0.9605	High Similarity	NPC65490
0.9605	High Similarity	NPC148014
0.9355	High Similarity	NPC18402
0.9351	High Similarity	NPC129603
0.8485	Intermediate Similarity	NPC284842
0.8313	Intermediate Similarity	NPC124657
0.8221	Intermediate Similarity	NPC160931
0.8221	Intermediate Similarity	NPC37205
0.8221	Intermediate Similarity	NPC147091
0.8221	Intermediate Similarity	NPC323443
0.8221	Intermediate Similarity	NPC180756
0.821	Intermediate Similarity	NPC2295
0.821	Intermediate Similarity	NPC477564
0.8204	Intermediate Similarity	NPC476002
0.8187	Intermediate Similarity	NPC207824
0.8187	Intermediate Similarity	NPC60538
0.8137	Intermediate Similarity	NPC274026
0.8121	Intermediate Similarity	NPC59028
0.8121	Intermediate Similarity	NPC92191
0.8107	Intermediate Similarity	NPC83198
0.8107	Intermediate Similarity	NPC204908
0.8086	Intermediate Similarity	NPC76213
0.8086	Intermediate Similarity	NPC277669
0.8072	Intermediate Similarity	NPC249274
0.8039	Intermediate Similarity	NPC160692
0.8023	Intermediate Similarity	NPC329969
0.8012	Intermediate Similarity	NPC470739
0.8012	Intermediate Similarity	NPC225597
0.8012	Intermediate Similarity	NPC477640
0.8	Intermediate Similarity	NPC475686
0.8	Intermediate Similarity	NPC58766
0.8	Intermediate Similarity	NPC266176
0.8	Intermediate Similarity	NPC290759
0.8	Intermediate Similarity	NPC82533
0.8	Intermediate Similarity	NPC158148
0.7989	Intermediate Similarity	NPC244554
0.7987	Intermediate Similarity	NPC294249
0.7965	Intermediate Similarity	NPC232386
0.7965	Intermediate Similarity	NPC152680
0.7965	Intermediate Similarity	NPC190783
0.7964	Intermediate Similarity	NPC215829
0.7964	Intermediate Similarity	NPC205167
0.7964	Intermediate Similarity	NPC97072
0.7953	Intermediate Similarity	NPC474475
0.795	Intermediate Similarity	NPC476151
0.7949	Intermediate Similarity	NPC253429
0.7933	Intermediate Similarity	NPC475754
0.7927	Intermediate Similarity	NPC82285
0.7927	Intermediate Similarity	NPC133011
0.7919	Intermediate Similarity	NPC49353
0.7898	Intermediate Similarity	NPC275132
0.7898	Intermediate Similarity	NPC476575
0.7874	Intermediate Similarity	NPC474470
0.7861	Intermediate Similarity	NPC2314
0.7861	Intermediate Similarity	NPC66341
0.7861	Intermediate Similarity	NPC192135
0.7861	Intermediate Similarity	NPC477020
0.7853	Intermediate Similarity	NPC477565
0.7853	Intermediate Similarity	NPC103379
0.7849	Intermediate Similarity	NPC69712
0.7849	Intermediate Similarity	NPC75958
0.7849	Intermediate Similarity	NPC26240
0.7849	Intermediate Similarity	NPC477562
0.7836	Intermediate Similarity	NPC100566
0.7836	Intermediate Similarity	NPC150879
0.7826	Intermediate Similarity	NPC185838
0.7826	Intermediate Similarity	NPC130926
0.7824	Intermediate Similarity	NPC39103
0.7824	Intermediate Similarity	NPC2770
0.7816	Intermediate Similarity	NPC477558
0.779	Intermediate Similarity	NPC117717
0.7784	Intermediate Similarity	NPC474507
0.7778	Intermediate Similarity	NPC476573
0.7778	Intermediate Similarity	NPC35627
0.7778	Intermediate Similarity	NPC81247
0.7778	Intermediate Similarity	NPC175890
0.7778	Intermediate Similarity	NPC48490
0.7778	Intermediate Similarity	NPC11296
0.7778	Intermediate Similarity	NPC82457
0.7778	Intermediate Similarity	NPC274661
0.7771	Intermediate Similarity	NPC475557
0.7771	Intermediate Similarity	NPC131204
0.7771	Intermediate Similarity	NPC301050
0.7771	Intermediate Similarity	NPC476577
0.7771	Intermediate Similarity	NPC148709
0.7771	Intermediate Similarity	NPC173416
0.7765	Intermediate Similarity	NPC320104
0.7753	Intermediate Similarity	NPC135772
0.7751	Intermediate Similarity	NPC4304
0.7746	Intermediate Similarity	NPC329911
0.7746	Intermediate Similarity	NPC311991
0.774	Intermediate Similarity	NPC477561
0.774	Intermediate Similarity	NPC305847
0.774	Intermediate Similarity	NPC312918
0.774	Intermediate Similarity	NPC155442
0.774	Intermediate Similarity	NPC476574
0.7735	Intermediate Similarity	NPC60295
0.7735	Intermediate Similarity	NPC191132
0.7733	Intermediate Similarity	NPC181653
0.7733	Intermediate Similarity	NPC190332
0.7733	Intermediate Similarity	NPC252960
0.773	Intermediate Similarity	NPC191376
0.773	Intermediate Similarity	NPC321505
0.773	Intermediate Similarity	NPC179825
0.7727	Intermediate Similarity	NPC160193
0.7727	Intermediate Similarity	NPC15919
0.7725	Intermediate Similarity	NPC78733
0.7714	Intermediate Similarity	NPC187678
0.7711	Intermediate Similarity	NPC114124
0.7709	Intermediate Similarity	NPC9867
0.7706	Intermediate Similarity	NPC60186
0.7701	Intermediate Similarity	NPC476331
0.7701	Intermediate Similarity	NPC108434
0.7701	Intermediate Similarity	NPC475215
0.7697	Intermediate Similarity	NPC302449
0.7688	Intermediate Similarity	NPC160570
0.7684	Intermediate Similarity	NPC126284
0.7684	Intermediate Similarity	NPC267408
0.7684	Intermediate Similarity	NPC243454
0.7684	Intermediate Similarity	NPC475479
0.7683	Intermediate Similarity	NPC428
0.7683	Intermediate Similarity	NPC476571
0.7683	Intermediate Similarity	NPC246587
0.7683	Intermediate Similarity	NPC59907
0.7683	Intermediate Similarity	NPC135538
0.7683	Intermediate Similarity	NPC37144
0.7683	Intermediate Similarity	NPC147390
0.7683	Intermediate Similarity	NPC24233
0.7679	Intermediate Similarity	NPC170503
0.7679	Intermediate Similarity	NPC126519
0.7679	Intermediate Similarity	NPC203784
0.7674	Intermediate Similarity	NPC13916
0.7674	Intermediate Similarity	NPC264850
0.767	Intermediate Similarity	NPC237044
0.7669	Intermediate Similarity	NPC473934
0.7667	Intermediate Similarity	NPC57036
0.7661	Intermediate Similarity	NPC218614
0.7661	Intermediate Similarity	NPC233650
0.765	Intermediate Similarity	NPC256124
0.7644	Intermediate Similarity	NPC152212
0.7644	Intermediate Similarity	NPC6152
0.764	Intermediate Similarity	NPC239584
0.763	Intermediate Similarity	NPC204947
0.7627	Intermediate Similarity	NPC118633
0.7627	Intermediate Similarity	NPC148693
0.7627	Intermediate Similarity	NPC474325
0.7627	Intermediate Similarity	NPC294790
0.7625	Intermediate Similarity	NPC314682
0.7624	Intermediate Similarity	NPC476576
0.7624	Intermediate Similarity	NPC186546
0.7619	Intermediate Similarity	NPC278799
0.7619	Intermediate Similarity	NPC207757
0.7619	Intermediate Similarity	NPC276588
0.7619	Intermediate Similarity	NPC54379
0.7619	Intermediate Similarity	NPC184026
0.7619	Intermediate Similarity	NPC172765
0.7619	Intermediate Similarity	NPC127674
0.7619	Intermediate Similarity	NPC110416
0.7619	Intermediate Similarity	NPC2413
0.7619	Intermediate Similarity	NPC39701
0.7619	Intermediate Similarity	NPC189266
0.7619	Intermediate Similarity	NPC193949
0.7619	Intermediate Similarity	NPC469817
0.7619	Intermediate Similarity	NPC5238
0.7619	Intermediate Similarity	NPC204828
0.7619	Intermediate Similarity	NPC249797
0.7619	Intermediate Similarity	NPC295691
0.7616	Intermediate Similarity	NPC247972
0.7616	Intermediate Similarity	NPC298486
0.7616	Intermediate Similarity	NPC24465
0.7616	Intermediate Similarity	NPC134858
0.7614	Intermediate Similarity	NPC304675
0.7613	Intermediate Similarity	NPC262641
0.7605	Intermediate Similarity	NPC148898
0.76	Intermediate Similarity	NPC65403
0.7598	Intermediate Similarity	NPC248642
0.7597	Intermediate Similarity	NPC172403
0.7586	Intermediate Similarity	NPC470324
0.7584	Intermediate Similarity	NPC99179
0.7584	Intermediate Similarity	NPC474745
0.7582	Intermediate Similarity	NPC281581
0.7582	Intermediate Similarity	NPC206900
0.758	Intermediate Similarity	NPC18842
0.7578	Intermediate Similarity	NPC474915
0.7578	Intermediate Similarity	NPC328750
0.7578	Intermediate Similarity	NPC323204
0.7578	Intermediate Similarity	NPC188163
0.7578	Intermediate Similarity	NPC213206
0.7572	Intermediate Similarity	NPC195392
0.7572	Intermediate Similarity	NPC86144
0.7572	Intermediate Similarity	NPC304659
0.7571	Intermediate Similarity	NPC241704
0.7571	Intermediate Similarity	NPC112575
0.7564	Intermediate Similarity	NPC329595
0.7564	Intermediate Similarity	NPC326599
0.7558	Intermediate Similarity	NPC475393

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 NPC124433 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	689
0.2-0.3	1051
0.3-0.4	2291
0.4-0.5	2489
0.5-0.6	1571
0.6-0.7	679
0.7-0.8	203
0.8-0.85	17
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9605	High Similarity	NPD2563	Approved
0.9605	High Similarity	NPD2560	Approved
0.9241	High Similarity	NPD6071	Discontinued
0.8263	Intermediate Similarity	NPD2970	Approved
0.8263	Intermediate Similarity	NPD2969	Approved
0.8107	Intermediate Similarity	NPD2489	Approved
0.8107	Intermediate Similarity	NPD27	Approved
0.8095	Intermediate Similarity	NPD3051	Approved
0.8089	Intermediate Similarity	NPD3060	Approved
0.8075	Intermediate Similarity	NPD6030	Approved
0.8075	Intermediate Similarity	NPD6031	Approved
0.8075	Intermediate Similarity	NPD5976	Discontinued
0.8025	Intermediate Similarity	NPD3686	Approved
0.8025	Intermediate Similarity	NPD3687	Approved
0.7975	Intermediate Similarity	NPD4162	Approved
0.7964	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7831	Phase 2
0.7964	Intermediate Similarity	NPD7833	Phase 2
0.7904	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD4773	Phase 2
0.7879	Intermediate Similarity	NPD4772	Phase 2
0.7875	Intermediate Similarity	NPD2677	Approved
0.784	Intermediate Similarity	NPD1424	Approved
0.7799	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7312	Approved
0.774	Intermediate Similarity	NPD7311	Approved
0.774	Intermediate Similarity	NPD7310	Approved
0.774	Intermediate Similarity	NPD7313	Approved
0.7697	Intermediate Similarity	NPD7309	Approved
0.7688	Intermediate Similarity	NPD4481	Phase 3
0.7688	Intermediate Similarity	NPD7153	Discontinued
0.7679	Intermediate Similarity	NPD2978	Approved
0.7679	Intermediate Similarity	NPD2977	Approved
0.7667	Intermediate Similarity	NPD7906	Approved
0.764	Intermediate Similarity	NPD4578	Approved
0.764	Intermediate Similarity	NPD4577	Approved
0.7619	Intermediate Similarity	NPD5720	Discontinued
0.7611	Intermediate Similarity	NPD4663	Approved
0.7602	Intermediate Similarity	NPD5709	Phase 3
0.7586	Intermediate Similarity	NPD2898	Approved
0.7578	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4666	Phase 3
0.7548	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5241	Discontinued
0.7546	Intermediate Similarity	NPD5160	Discontinued
0.7531	Intermediate Similarity	NPD4236	Phase 3
0.7531	Intermediate Similarity	NPD4237	Approved
0.7516	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4584	Approved
0.75	Intermediate Similarity	NPD8054	Approved
0.75	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8053	Approved
0.75	Intermediate Similarity	NPD2154	Approved
0.75	Intermediate Similarity	NPD2156	Approved
0.75	Intermediate Similarity	NPD2155	Approved
0.7484	Intermediate Similarity	NPD3054	Approved
0.7484	Intermediate Similarity	NPD3052	Approved
0.7471	Intermediate Similarity	NPD5772	Approved
0.7471	Intermediate Similarity	NPD5773	Approved
0.747	Intermediate Similarity	NPD7526	Approved
0.747	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD52	Approved
0.7468	Intermediate Similarity	NPD2238	Phase 2
0.7458	Intermediate Similarity	NPD8156	Discontinued
0.7455	Intermediate Similarity	NPD1774	Approved
0.7453	Intermediate Similarity	NPD2161	Phase 2
0.7452	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5177	Phase 3
0.7412	Intermediate Similarity	NPD7298	Approved
0.741	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4123	Phase 3
0.741	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8252	Approved
0.7401	Intermediate Similarity	NPD8099	Discontinued
0.7401	Intermediate Similarity	NPD8251	Approved
0.7381	Intermediate Similarity	NPD4210	Discontinued
0.7375	Intermediate Similarity	NPD2653	Approved
0.7368	Intermediate Similarity	NPD4585	Approved
0.736	Intermediate Similarity	NPD4873	Discontinued
0.7353	Intermediate Similarity	NPD6072	Discontinued
0.7346	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1336	Approved
0.7333	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6107	Approved
0.7305	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7019	Approved
0.7305	Intermediate Similarity	NPD2874	Phase 2
0.7305	Intermediate Similarity	NPD7020	Approved
0.7301	Intermediate Similarity	NPD1375	Discontinued
0.7297	Intermediate Similarity	NPD2488	Approved
0.7297	Intermediate Similarity	NPD2490	Approved
0.7296	Intermediate Similarity	NPD3163	Approved
0.7296	Intermediate Similarity	NPD3162	Approved
0.7296	Intermediate Similarity	NPD2674	Phase 3
0.7296	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4678	Approved
0.7294	Intermediate Similarity	NPD4675	Approved
0.7289	Intermediate Similarity	NPD7124	Phase 2
0.7278	Intermediate Similarity	NPD3180	Approved
0.7278	Intermediate Similarity	NPD3179	Approved
0.7278	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6331	Phase 2
0.7263	Intermediate Similarity	NPD42	Phase 2
0.7263	Intermediate Similarity	NPD6042	Phase 2
0.7257	Intermediate Similarity	NPD3365	Discontinued
0.7253	Intermediate Similarity	NPD2971	Approved
0.7253	Intermediate Similarity	NPD2968	Approved
0.725	Intermediate Similarity	NPD3061	Approved
0.725	Intermediate Similarity	NPD3059	Approved
0.725	Intermediate Similarity	NPD3062	Approved
0.725	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6087	Phase 1
0.7241	Intermediate Similarity	NPD4055	Discovery
0.7238	Intermediate Similarity	NPD7039	Approved
0.7238	Intermediate Similarity	NPD7038	Approved
0.7235	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD601	Approved
0.7233	Intermediate Similarity	NPD598	Approved
0.7233	Intermediate Similarity	NPD597	Approved
0.7229	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6895	Approved
0.7222	Intermediate Similarity	NPD6896	Approved
0.7212	Intermediate Similarity	NPD2460	Phase 3
0.7212	Intermediate Similarity	NPD2459	Approved
0.7212	Intermediate Similarity	NPD2458	Approved
0.7209	Intermediate Similarity	NPD5722	Discontinued
0.7202	Intermediate Similarity	NPD3536	Discontinued
0.7197	Intermediate Similarity	NPD558	Phase 2
0.7197	Intermediate Similarity	NPD9620	Approved
0.7197	Intermediate Similarity	NPD9621	Approved
0.7197	Intermediate Similarity	NPD9619	Approved
0.7196	Intermediate Similarity	NPD2974	Approved
0.7196	Intermediate Similarity	NPD2973	Approved
0.7196	Intermediate Similarity	NPD2975	Approved
0.7188	Intermediate Similarity	NPD3531	Approved
0.7188	Intermediate Similarity	NPD3530	Approved
0.7188	Intermediate Similarity	NPD1132	Approved
0.7188	Intermediate Similarity	NPD3532	Approved
0.7188	Intermediate Similarity	NPD1136	Approved
0.7188	Intermediate Similarity	NPD1130	Approved
0.7186	Intermediate Similarity	NPD6667	Approved
0.7186	Intermediate Similarity	NPD3122	Phase 3
0.7186	Intermediate Similarity	NPD6666	Approved
0.7184	Intermediate Similarity	NPD6788	Approved
0.7175	Intermediate Similarity	NPD4166	Phase 2
0.7161	Intermediate Similarity	NPD2231	Phase 2
0.7161	Intermediate Similarity	NPD2235	Phase 2
0.716	Intermediate Similarity	NPD823	Approved
0.716	Intermediate Similarity	NPD5314	Approved
0.716	Intermediate Similarity	NPD6090	Discontinued
0.716	Intermediate Similarity	NPD817	Approved
0.7151	Intermediate Similarity	NPD2845	Phase 2
0.7151	Intermediate Similarity	NPD2843	Phase 2
0.7151	Intermediate Similarity	NPD3489	Phase 3
0.7143	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4017	Approved
0.7135	Intermediate Similarity	NPD3452	Approved
0.7135	Intermediate Similarity	NPD2494	Approved
0.7135	Intermediate Similarity	NPD2493	Approved
0.7135	Intermediate Similarity	NPD3450	Approved
0.7134	Intermediate Similarity	NPD1794	Approved
0.7134	Intermediate Similarity	NPD1818	Approved
0.7134	Intermediate Similarity	NPD1819	Approved
0.7134	Intermediate Similarity	NPD3156	Discontinued
0.7134	Intermediate Similarity	NPD1820	Approved
0.7134	Intermediate Similarity	NPD1817	Approved
0.7126	Intermediate Similarity	NPD3692	Discontinued
0.7125	Intermediate Similarity	NPD3145	Approved
0.7125	Intermediate Similarity	NPD3144	Approved
0.7124	Intermediate Similarity	NPD3049	Approved
0.712	Intermediate Similarity	NPD6853	Approved
0.712	Intermediate Similarity	NPD6851	Approved
0.7118	Intermediate Similarity	NPD3640	Phase 3
0.7118	Intermediate Similarity	NPD3641	Approved
0.7118	Intermediate Similarity	NPD3639	Approved
0.7117	Intermediate Similarity	NPD6111	Discontinued
0.7112	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3384	Approved
0.711	Intermediate Similarity	NPD3382	Approved
0.711	Intermediate Similarity	NPD3383	Approved
0.7108	Intermediate Similarity	NPD5061	Approved
0.7108	Intermediate Similarity	NPD5062	Approved
0.7107	Intermediate Similarity	NPD600	Approved
0.7107	Intermediate Similarity	NPD596	Approved
0.7099	Intermediate Similarity	NPD1341	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD3057	Approved
0.7088	Intermediate Similarity	NPD6297	Approved
0.7083	Intermediate Similarity	NPD4580	Approved
0.7083	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3845	Phase 1
0.7081	Intermediate Similarity	NPD6405	Approved
0.7081	Intermediate Similarity	NPD4474	Approved
0.7081	Intermediate Similarity	NPD4475	Approved
0.7081	Intermediate Similarity	NPD6407	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