NPASS Compound

Structure

NPC187678 OpenBabel07101718322D 23 27 0 0 1 0 0 0 0 0999 V2000 -1.1199 -1.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1960 2.4216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6327 3.2478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4599 3.0479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4599 1.4217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1199 3.1484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4153 2.2348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7557 2.6414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5843 1.6305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7557 1.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1641 2.6414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1641 1.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1199 1.3213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3571 1.9679 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7628 0.6466 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9414 0.3373 0.0000 C 0 0 1 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 0.3272 2.9674 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.7042 0.3093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7042 -0.3093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1786 -0.9839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9374 2.8926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9374 1.5770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 1 0 0 0 0 2 9 2 0 0 0 0 3 18 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 18 1 0 0 0 0 7 22 1 0 0 0 0 7 23 1 0 0 0 0 8 10 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 11 12 2 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 10 1 6 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 18 1 1 0 0 0 15 17 1 0 0 0 0 15 19 1 6 0 0 0 16 17 1 0 0 0 0 16 20 1 6 0 0 0 17 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	317.13
Volume:	304.208
LogP:	1.176
LogD:	1.312
LogS:	-1.904
# Rotatable Bonds:	1
TPSA:	71.39
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	4.437
Fsp3:	0.529
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:	-5.072
MDCK Permeability:	5.087951649329625e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.202
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.166
30% Bioavailability (F30%):	0.349

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97
Plasma Protein Binding (PPB):	79.85587310791016%
Volume Distribution (VD):	1.285
Pgp-substrate:	29.99493408203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.515
CYP1A2-substrate:	0.837
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.37
CYP2D6-inhibitor:	0.854
CYP2D6-substrate:	0.53
CYP3A4-inhibitor:	0.191
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	12.707
Half-life (T1/2):	0.611

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.34
AMES Toxicity:	0.134
Rat Oral Acute Toxicity:	0.875
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.105
Carcinogencity:	0.337
Eye Corrosion:	0.013
Eye Irritation:	0.017
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC187678

Natural Product ID:	NPC187678
*Common Name:**	Ungiminorine
IUPAC Name:	n.a.
Synonyms:	Ungiminorine
Standard InCHIKey:	ZQLQBAUVRGDBJL-BIVLZKPYSA-N
Standard InCHI:	InChI=1S/C17H19NO5/c1-21-17-15(19)9-2-3-18-6-8-4-11-12(23-7-22-11)5-10(8)13(14(9)18)16(17)20/h2,4-5,13-17,19-20H,3,6-7H2,1H3/t13-,14+,15+,16-,17-/m0/s1
SMILES:	CO[C@H]1[C@H](O)C2=CCN3[C@H]2[C@@H]([C@@H]1O)c1cc2OCOc2cc1C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497276
PubChem CID:	10425948
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
NPO32885	narcissus ‘sir winston churchill'	n.a.	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869205]

☑ 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
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	86000.0	nM	PMID[565824]

☑ 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 NPC187678 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	301
0.1-0.2	1316
0.2-0.3	4598
0.3-0.4	11792
0.4-0.5	7313
0.5-0.6	12132
0.6-0.7	4231
0.7-0.8	764
0.8-0.85	188
0.85-0.9	55
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9325	High Similarity	NPC311991
0.9321	High Similarity	NPC100566
0.9277	High Similarity	NPC15919
0.9202	High Similarity	NPC190332
0.9202	High Similarity	NPC181653
0.9048	High Similarity	NPC148693
0.9048	High Similarity	NPC294790
0.9048	High Similarity	NPC118633
0.9036	High Similarity	NPC65403
0.9018	High Similarity	NPC320104
0.9006	High Similarity	NPC9867
0.8988	High Similarity	NPC237044
0.8935	High Similarity	NPC474325
0.8929	High Similarity	NPC304675
0.8882	High Similarity	NPC474745
0.8869	High Similarity	NPC2314
0.8837	High Similarity	NPC474746
0.8837	High Similarity	NPC475981
0.881	High Similarity	NPC470739
0.881	High Similarity	NPC477640
0.881	High Similarity	NPC225597
0.8802	High Similarity	NPC475686
0.8802	High Similarity	NPC82533
0.8802	High Similarity	NPC266176
0.8802	High Similarity	NPC158148
0.8802	High Similarity	NPC58766
0.8802	High Similarity	NPC290759
0.878	High Similarity	NPC205167
0.878	High Similarity	NPC249274
0.8772	High Similarity	NPC244554
0.875	High Similarity	NPC474475
0.8706	High Similarity	NPC49353
0.8683	High Similarity	NPC476002
0.8671	High Similarity	NPC275132
0.8667	High Similarity	NPC97072
0.8667	High Similarity	NPC215829
0.8667	High Similarity	NPC4304
0.8642	High Similarity	NPC148898
0.8639	High Similarity	NPC75958
0.8631	High Similarity	NPC57812
0.8631	High Similarity	NPC474324
0.8629	High Similarity	NPC230098
0.8623	High Similarity	NPC232514
0.8623	High Similarity	NPC238530
0.8623	High Similarity	NPC276944
0.8606	High Similarity	NPC92191
0.8606	High Similarity	NPC111485
0.8606	High Similarity	NPC59028
0.8596	High Similarity	NPC128560
0.8596	High Similarity	NPC229166
0.8596	High Similarity	NPC199465
0.858	High Similarity	NPC475845
0.8563	High Similarity	NPC248642
0.8555	High Similarity	NPC126284
0.8547	High Similarity	NPC474470
0.8529	High Similarity	NPC474708
0.8523	High Similarity	NPC214116
0.8519	High Similarity	NPC274026
0.8514	High Similarity	NPC156576
0.8509	High Similarity	NPC475959
0.8497	Intermediate Similarity	NPC320223
0.8497	Intermediate Similarity	NPC114364
0.8485	Intermediate Similarity	NPC146288
0.8424	Intermediate Similarity	NPC216459
0.8424	Intermediate Similarity	NPC78733
0.8424	Intermediate Similarity	NPC41178
0.8424	Intermediate Similarity	NPC138487
0.8415	Intermediate Similarity	NPC210148
0.8415	Intermediate Similarity	NPC133011
0.8415	Intermediate Similarity	NPC233029
0.8415	Intermediate Similarity	NPC82285
0.8412	Intermediate Similarity	NPC210918
0.8402	Intermediate Similarity	NPC180306
0.8402	Intermediate Similarity	NPC16805
0.8402	Intermediate Similarity	NPC24465
0.8402	Intermediate Similarity	NPC302527
0.8402	Intermediate Similarity	NPC167546
0.8373	Intermediate Similarity	NPC147091
0.8373	Intermediate Similarity	NPC234392
0.8373	Intermediate Similarity	NPC31311
0.8372	Intermediate Similarity	NPC149090
0.8372	Intermediate Similarity	NPC19520
0.8353	Intermediate Similarity	NPC476432
0.8353	Intermediate Similarity	NPC13916
0.8353	Intermediate Similarity	NPC264850
0.8353	Intermediate Similarity	NPC24264
0.8352	Intermediate Similarity	NPC116284
0.8324	Intermediate Similarity	NPC82763
0.8304	Intermediate Similarity	NPC304846
0.8304	Intermediate Similarity	NPC247389
0.8304	Intermediate Similarity	NPC252960
0.8304	Intermediate Similarity	NPC298979
0.8295	Intermediate Similarity	NPC476574
0.8295	Intermediate Similarity	NPC155442
0.8295	Intermediate Similarity	NPC477561
0.8295	Intermediate Similarity	NPC312918
0.8294	Intermediate Similarity	NPC89199
0.8294	Intermediate Similarity	NPC54125
0.8294	Intermediate Similarity	NPC231198
0.8294	Intermediate Similarity	NPC225774
0.8282	Intermediate Similarity	NPC59907
0.8282	Intermediate Similarity	NPC428
0.8282	Intermediate Similarity	NPC37144
0.8282	Intermediate Similarity	NPC24233
0.8282	Intermediate Similarity	NPC135538
0.8282	Intermediate Similarity	NPC147390
0.8282	Intermediate Similarity	NPC476571
0.8282	Intermediate Similarity	NPC246587
0.8268	Intermediate Similarity	NPC186546
0.8268	Intermediate Similarity	NPC476576
0.8256	Intermediate Similarity	NPC83198
0.8256	Intermediate Similarity	NPC204908
0.8249	Intermediate Similarity	NPC233718
0.8246	Intermediate Similarity	NPC219341
0.8235	Intermediate Similarity	NPC218614
0.8232	Intermediate Similarity	NPC24260
0.8232	Intermediate Similarity	NPC117717
0.8232	Intermediate Similarity	NPC103379
0.8232	Intermediate Similarity	NPC477565
0.8221	Intermediate Similarity	NPC476151
0.8221	Intermediate Similarity	NPC191376
0.8221	Intermediate Similarity	NPC321505
0.8221	Intermediate Similarity	NPC179825
0.8212	Intermediate Similarity	NPC57036
0.821	Intermediate Similarity	NPC185838
0.821	Intermediate Similarity	NPC130926
0.8204	Intermediate Similarity	NPC249797
0.8204	Intermediate Similarity	NPC184026
0.8204	Intermediate Similarity	NPC469817
0.8204	Intermediate Similarity	NPC295691
0.8204	Intermediate Similarity	NPC110416
0.8204	Intermediate Similarity	NPC276588
0.8204	Intermediate Similarity	NPC278799
0.8204	Intermediate Similarity	NPC5238
0.8204	Intermediate Similarity	NPC39701
0.8204	Intermediate Similarity	NPC172765
0.8204	Intermediate Similarity	NPC127674
0.8204	Intermediate Similarity	NPC189266
0.8204	Intermediate Similarity	NPC54379
0.8204	Intermediate Similarity	NPC2413
0.8204	Intermediate Similarity	NPC193949
0.8204	Intermediate Similarity	NPC207757
0.8204	Intermediate Similarity	NPC204828
0.8202	Intermediate Similarity	NPC135772
0.8198	Intermediate Similarity	NPC301189
0.8198	Intermediate Similarity	NPC150879
0.8198	Intermediate Similarity	NPC298186
0.8192	Intermediate Similarity	NPC474607
0.8187	Intermediate Similarity	NPC253043
0.8187	Intermediate Similarity	NPC196447
0.8187	Intermediate Similarity	NPC136508
0.8187	Intermediate Similarity	NPC477563
0.8187	Intermediate Similarity	NPC247972
0.8187	Intermediate Similarity	NPC78222
0.8187	Intermediate Similarity	NPC212794
0.8187	Intermediate Similarity	NPC13504
0.8187	Intermediate Similarity	NPC306843
0.8187	Intermediate Similarity	NPC96603
0.8182	Intermediate Similarity	NPC220858
0.8182	Intermediate Similarity	NPC88249
0.8182	Intermediate Similarity	NPC97221
0.8182	Intermediate Similarity	NPC151895
0.8182	Intermediate Similarity	NPC192768
0.8166	Intermediate Similarity	NPC477080
0.8161	Intermediate Similarity	NPC239775
0.8146	Intermediate Similarity	NPC474650
0.8146	Intermediate Similarity	NPC476575
0.8129	Intermediate Similarity	NPC324144
0.8118	Intermediate Similarity	NPC266753
0.8118	Intermediate Similarity	NPC165797
0.8118	Intermediate Similarity	NPC477559
0.8118	Intermediate Similarity	NPC232924
0.8118	Intermediate Similarity	NPC160298
0.8118	Intermediate Similarity	NPC306902
0.8114	Intermediate Similarity	NPC152680
0.8114	Intermediate Similarity	NPC110374
0.8114	Intermediate Similarity	NPC228040
0.8114	Intermediate Similarity	NPC190783
0.8114	Intermediate Similarity	NPC289743
0.8114	Intermediate Similarity	NPC232386
0.8107	Intermediate Similarity	NPC129603
0.8107	Intermediate Similarity	NPC475326
0.8103	Intermediate Similarity	NPC6152
0.8095	Intermediate Similarity	NPC93593
0.8092	Intermediate Similarity	NPC12053
0.8092	Intermediate Similarity	NPC117188
0.8092	Intermediate Similarity	NPC205421
0.8092	Intermediate Similarity	NPC145832
0.8092	Intermediate Similarity	NPC158376
0.8092	Intermediate Similarity	NPC474931
0.8092	Intermediate Similarity	NPC81218
0.8092	Intermediate Similarity	NPC306555
0.8084	Intermediate Similarity	NPC223124
0.8077	Intermediate Similarity	NPC475754
0.8075	Intermediate Similarity	NPC328750
0.8075	Intermediate Similarity	NPC213206
0.8075	Intermediate Similarity	NPC188163
0.8075	Intermediate Similarity	NPC474915
0.8068	Intermediate Similarity	NPC477558
0.8068	Intermediate Similarity	NPC329969

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 NPC187678 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	654
0.2-0.3	1001
0.3-0.4	2393
0.4-0.5	2600
0.5-0.6	1627
0.6-0.7	563
0.7-0.8	114
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8198	Intermediate Similarity	NPD2970	Approved
0.8198	Intermediate Similarity	NPD2969	Approved
0.8144	Intermediate Similarity	NPD4772	Phase 2
0.8144	Intermediate Similarity	NPD4773	Phase 2
0.814	Intermediate Similarity	NPD3051	Approved
0.8075	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD27	Approved
0.8046	Intermediate Similarity	NPD2489	Approved
0.8035	Intermediate Similarity	NPD6071	Discontinued
0.8	Intermediate Similarity	NPD2560	Approved
0.8	Intermediate Similarity	NPD4584	Approved
0.8	Intermediate Similarity	NPD2563	Approved
0.7857	Intermediate Similarity	NPD4663	Approved
0.7845	Intermediate Similarity	NPD8054	Approved
0.7845	Intermediate Similarity	NPD8053	Approved
0.7836	Intermediate Similarity	NPD2977	Approved
0.7836	Intermediate Similarity	NPD2978	Approved
0.7836	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD7906	Approved
0.779	Intermediate Similarity	NPD7312	Approved
0.779	Intermediate Similarity	NPD7311	Approved
0.779	Intermediate Similarity	NPD7310	Approved
0.779	Intermediate Similarity	NPD4578	Approved
0.779	Intermediate Similarity	NPD7313	Approved
0.779	Intermediate Similarity	NPD4577	Approved
0.7747	Intermediate Similarity	NPD7309	Approved
0.774	Intermediate Similarity	NPD4481	Phase 3
0.7711	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5241	Discontinued
0.7709	Intermediate Similarity	NPD8156	Discontinued
0.7696	Intermediate Similarity	NPD5006	Approved
0.7696	Intermediate Similarity	NPD5005	Approved
0.7672	Intermediate Similarity	NPD4420	Approved
0.7654	Intermediate Similarity	NPD8251	Approved
0.7654	Intermediate Similarity	NPD8099	Discontinued
0.7654	Intermediate Similarity	NPD8252	Approved
0.7627	Intermediate Similarity	NPD4010	Discontinued
0.759	Intermediate Similarity	NPD4236	Phase 3
0.759	Intermediate Similarity	NPD4237	Approved
0.7588	Intermediate Similarity	NPD3639	Approved
0.7588	Intermediate Similarity	NPD3640	Phase 3
0.7588	Intermediate Similarity	NPD3641	Approved
0.7572	Intermediate Similarity	NPD7298	Approved
0.7571	Intermediate Similarity	NPD6107	Approved
0.7566	Intermediate Similarity	NPD5582	Discontinued
0.756	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD6788	Approved
0.7542	Intermediate Similarity	NPD2898	Approved
0.7531	Intermediate Similarity	NPD2238	Phase 2
0.75	Intermediate Similarity	NPD4017	Approved
0.75	Intermediate Similarity	NPD7296	Approved
0.75	Intermediate Similarity	NPD7281	Phase 3
0.75	Intermediate Similarity	NPD7280	Phase 3
0.75	Intermediate Similarity	NPD5604	Discontinued
0.7485	Intermediate Similarity	NPD5177	Phase 3
0.7471	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5772	Approved
0.7429	Intermediate Similarity	NPD5773	Approved
0.7416	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7833	Phase 2
0.7401	Intermediate Similarity	NPD7831	Phase 2
0.7399	Intermediate Similarity	NPD4005	Discontinued
0.7384	Intermediate Similarity	NPD6031	Approved
0.7384	Intermediate Similarity	NPD6030	Approved
0.7358	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD2488	Approved
0.7354	Intermediate Similarity	NPD2490	Approved
0.735	Intermediate Similarity	NPD7827	Phase 1
0.7346	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD5312	Approved
0.7322	Intermediate Similarity	NPD5313	Approved
0.7303	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD3452	Approved
0.7282	Intermediate Similarity	NPD2494	Approved
0.7282	Intermediate Similarity	NPD3450	Approved
0.7282	Intermediate Similarity	NPD2493	Approved
0.7278	Intermediate Similarity	NPD3060	Approved
0.7267	Intermediate Similarity	NPD1424	Approved
0.7259	Intermediate Similarity	NPD4583	Approved
0.7259	Intermediate Similarity	NPD4582	Approved
0.7254	Intermediate Similarity	NPD2975	Approved
0.7254	Intermediate Similarity	NPD2973	Approved
0.7254	Intermediate Similarity	NPD2974	Approved
0.7249	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7007	Discovery
0.7241	Intermediate Similarity	NPD4210	Discontinued
0.7238	Intermediate Similarity	NPD4166	Phase 2
0.7231	Intermediate Similarity	NPD4580	Approved
0.7219	Intermediate Similarity	NPD2971	Approved
0.7219	Intermediate Similarity	NPD2968	Approved
0.7209	Intermediate Similarity	NPD2421	Approved
0.7209	Intermediate Similarity	NPD2420	Approved
0.7208	Intermediate Similarity	NPD4002	Approved
0.7208	Intermediate Similarity	NPD4004	Approved
0.7207	Intermediate Similarity	NPD4055	Discovery
0.716	Intermediate Similarity	NPD1375	Discontinued
0.7157	Intermediate Similarity	NPD7047	Phase 3
0.7152	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6297	Approved
0.7151	Intermediate Similarity	NPD7124	Phase 2
0.7115	Intermediate Similarity	NPD6997	Phase 2
0.7101	Intermediate Similarity	NPD2161	Phase 2
0.7101	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5718	Phase 2
0.709	Intermediate Similarity	NPD6853	Approved
0.709	Intermediate Similarity	NPD6851	Approved
0.7086	Intermediate Similarity	NPD4727	Phase 1
0.7079	Intermediate Similarity	NPD3382	Approved
0.7079	Intermediate Similarity	NPD3384	Approved
0.7079	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3383	Approved
0.7079	Intermediate Similarity	NPD37	Approved
0.7076	Intermediate Similarity	NPD4162	Approved
0.7068	Intermediate Similarity	NPD6842	Approved
0.7068	Intermediate Similarity	NPD6841	Approved
0.7068	Intermediate Similarity	NPD6843	Phase 3
0.7056	Intermediate Similarity	NPD4967	Phase 2
0.7056	Intermediate Similarity	NPD4966	Approved
0.7056	Intermediate Similarity	NPD4965	Approved
0.7056	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1753	Discontinued
0.7037	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3124	Discontinued
0.7	Intermediate Similarity	NPD4040	Phase 1
0.6995	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2677	Approved
0.6985	Remote Similarity	NPD3057	Approved
0.6984	Remote Similarity	NPD7549	Discontinued
0.6984	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6896	Approved
0.6982	Remote Similarity	NPD6895	Approved
0.6978	Remote Similarity	NPD6234	Discontinued
0.6977	Remote Similarity	NPD6674	Discontinued
0.6977	Remote Similarity	NPD6625	Approved
0.6971	Remote Similarity	NPD4123	Phase 3
0.697	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4678	Approved
0.6966	Remote Similarity	NPD4675	Approved
0.6957	Remote Similarity	NPD3705	Approved
0.6954	Remote Similarity	NPD3845	Phase 1
0.6954	Remote Similarity	NPD6667	Approved
0.6954	Remote Similarity	NPD6666	Approved
0.6946	Remote Similarity	NPD2674	Phase 3
0.6943	Remote Similarity	NPD2843	Phase 2
0.6943	Remote Similarity	NPD2845	Phase 2
0.6941	Remote Similarity	NPD4108	Discontinued
0.694	Remote Similarity	NPD5677	Discontinued
0.6932	Remote Similarity	NPD6090	Discontinued
0.6923	Remote Similarity	NPD2492	Phase 1
0.6919	Remote Similarity	NPD8095	Phase 1
0.6919	Remote Similarity	NPD6687	Approved
0.6919	Remote Similarity	NPD6688	Approved
0.6914	Remote Similarity	NPD2230	Approved
0.6914	Remote Similarity	NPD2233	Approved
0.6914	Remote Similarity	NPD2232	Approved
0.6907	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5977	Approved
0.6906	Remote Similarity	NPD5978	Approved
0.6905	Remote Similarity	NPD3109	Approved
0.6905	Remote Similarity	NPD3110	Approved
0.6902	Remote Similarity	NPD7802	Discontinued
0.69	Remote Similarity	NPD3533	Approved
0.69	Remote Similarity	NPD2972	Approved
0.6898	Remote Similarity	NPD6723	Discontinued
0.6898	Remote Similarity	NPD7228	Approved
0.6897	Remote Similarity	NPD5160	Discontinued
0.6893	Remote Similarity	NPD5976	Discontinued
0.6893	Remote Similarity	NPD2122	Discontinued
0.6886	Remote Similarity	NPD3145	Approved
0.6886	Remote Similarity	NPD3144	Approved
0.6882	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6111	Discontinued
0.6878	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7497	Discontinued
0.686	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3686	Approved
0.6854	Remote Similarity	NPD3687	Approved
0.6851	Remote Similarity	NPD4585	Approved
0.6848	Remote Similarity	NPD4666	Phase 3
0.6845	Remote Similarity	NPD4474	Approved
0.6845	Remote Similarity	NPD4475	Approved
0.684	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6331	Phase 2
0.6839	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5754	Discontinued
0.6836	Remote Similarity	NPD52	Approved
0.6836	Remote Similarity	NPD7526	Approved
0.6836	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7527	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