NPASS Compound

Structure

NPC21885 OpenBabel07101719242D 24 27 0 0 1 0 0 0 0 0999 V2000 2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3585 -3.4450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1421 -1.7695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3766 -2.0438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6849 -1.6163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1579 -2.1547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2721 -3.0383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 24 1 0 0 0 0 3 4 1 0 0 0 0 3 9 1 0 0 0 0 4 21 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 18 1 0 0 0 0 7 11 2 0 0 0 0 7 18 1 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 12 8 1 6 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 22 2 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.96
Volume:	345.774
LogP:	2.613
LogD:	2.273
LogS:	-2.779
# Rotatable Bonds:	1
TPSA:	49.77
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.702
Synthetic Accessibility Score:	4.371
Fsp3:	0.389
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.963
MDCK Permeability:	1.9331491785123944e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.853
30% Bioavailability (F30%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	80.59766387939453%
Volume Distribution (VD):	2.188
Pgp-substrate:	24.249879837036133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.396
CYP1A2-substrate:	0.91
CYP2C19-inhibitor:	0.908
CYP2C19-substrate:	0.904
CYP2C9-inhibitor:	0.592
CYP2C9-substrate:	0.718
CYP2D6-inhibitor:	0.905
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.514
CYP3A4-substrate:	0.802

ADMET: Excretion

Clearance (CL):	2.82
Half-life (T1/2):	0.53

ADMET: Toxicity

hERG Blockers:	0.168
Human Hepatotoxicity (H-HT):	0.719
Drug-inuced Liver Injury (DILI):	0.225
AMES Toxicity:	0.866
Rat Oral Acute Toxicity:	0.586
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.513
Carcinogencity:	0.965
Eye Corrosion:	0.004
Eye Irritation:	0.013
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: NPC21885

Natural Product ID:	NPC21885
*Common Name:**	Saldedine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CHIIYNHRBKMNTF-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C18H17Br2NO3/c1-21-4-3-9-5-13(24-2)17(23)15-14(9)12(21)8-18(15)6-10(19)16(22)11(20)7-18/h5-7,12,23H,3-4,8H2,1-2H3/t12-/m0/s1
SMILES:	CN1CCc2cc(c(c3c2[C@@H]1CC13C=C(C(=O)C(=C1)Br)Br)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563942
PubChem CID:	45273137
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002660] Proaporphines

*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
NPO33411	madagascan tunicate	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19216520]

☑ 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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	4.4	uM	PMID[494313]

☑ 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 NPC21885 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	298
0.1-0.2	1667
0.2-0.3	6289
0.3-0.4	12002
0.4-0.5	6443
0.5-0.6	13416
0.6-0.7	2013
0.7-0.8	508
0.8-0.85	54
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9506	High Similarity	NPC470324
0.939	High Similarity	NPC476331
0.9074	High Similarity	NPC118804
0.8743	High Similarity	NPC2770
0.8743	High Similarity	NPC39103
0.8412	Intermediate Similarity	NPC3375
0.8412	Intermediate Similarity	NPC255607
0.8343	Intermediate Similarity	NPC226428
0.8274	Intermediate Similarity	NPC147091
0.8242	Intermediate Similarity	NPC103379
0.8242	Intermediate Similarity	NPC477565
0.8232	Intermediate Similarity	NPC191376
0.8232	Intermediate Similarity	NPC321505
0.8232	Intermediate Similarity	NPC179825
0.8182	Intermediate Similarity	NPC135538
0.8182	Intermediate Similarity	NPC428
0.8182	Intermediate Similarity	NPC476571
0.8182	Intermediate Similarity	NPC24233
0.8182	Intermediate Similarity	NPC147390
0.8182	Intermediate Similarity	NPC246587
0.8129	Intermediate Similarity	NPC27410
0.8129	Intermediate Similarity	NPC166014
0.8121	Intermediate Similarity	NPC476151
0.811	Intermediate Similarity	NPC185838
0.8107	Intermediate Similarity	NPC207757
0.8107	Intermediate Similarity	NPC204828
0.8107	Intermediate Similarity	NPC249797
0.8107	Intermediate Similarity	NPC5238
0.8107	Intermediate Similarity	NPC295691
0.8107	Intermediate Similarity	NPC110416
0.8107	Intermediate Similarity	NPC469817
0.8107	Intermediate Similarity	NPC193949
0.8107	Intermediate Similarity	NPC54379
0.8107	Intermediate Similarity	NPC278799
0.8107	Intermediate Similarity	NPC39701
0.8107	Intermediate Similarity	NPC172765
0.8107	Intermediate Similarity	NPC127674
0.8107	Intermediate Similarity	NPC189266
0.8107	Intermediate Similarity	NPC276588
0.8107	Intermediate Similarity	NPC184026
0.8107	Intermediate Similarity	NPC2413
0.8095	Intermediate Similarity	NPC133011
0.8095	Intermediate Similarity	NPC82285
0.8084	Intermediate Similarity	NPC220858
0.8084	Intermediate Similarity	NPC192768
0.8084	Intermediate Similarity	NPC97221
0.8084	Intermediate Similarity	NPC88249
0.8084	Intermediate Similarity	NPC151895
0.8045	Intermediate Similarity	NPC32154
0.8035	Intermediate Similarity	NPC324144
0.8023	Intermediate Similarity	NPC205167
0.8023	Intermediate Similarity	NPC249274
0.7989	Intermediate Similarity	NPC78222
0.7989	Intermediate Similarity	NPC136508
0.7989	Intermediate Similarity	NPC253043
0.7989	Intermediate Similarity	NPC477563
0.7989	Intermediate Similarity	NPC306843
0.7989	Intermediate Similarity	NPC96603
0.7989	Intermediate Similarity	NPC212794
0.7989	Intermediate Similarity	NPC13504
0.7989	Intermediate Similarity	NPC196447
0.795	Intermediate Similarity	NPC131204
0.795	Intermediate Similarity	NPC301050
0.7943	Intermediate Similarity	NPC124657
0.7941	Intermediate Similarity	NPC477564
0.7941	Intermediate Similarity	NPC2295
0.7933	Intermediate Similarity	NPC241704
0.7929	Intermediate Similarity	NPC277669
0.7929	Intermediate Similarity	NPC85747
0.7929	Intermediate Similarity	NPC8337
0.7929	Intermediate Similarity	NPC476579
0.7929	Intermediate Similarity	NPC76213
0.7898	Intermediate Similarity	NPC306555
0.7898	Intermediate Similarity	NPC12053
0.7898	Intermediate Similarity	NPC145832
0.7898	Intermediate Similarity	NPC474931
0.7898	Intermediate Similarity	NPC81218
0.7898	Intermediate Similarity	NPC158376
0.7898	Intermediate Similarity	NPC117188
0.7898	Intermediate Similarity	NPC205421
0.7886	Intermediate Similarity	NPC276944
0.7886	Intermediate Similarity	NPC238530
0.7886	Intermediate Similarity	NPC232514
0.7882	Intermediate Similarity	NPC223124
0.7882	Intermediate Similarity	NPC37272
0.787	Intermediate Similarity	NPC274026
0.7861	Intermediate Similarity	NPC111485
0.7849	Intermediate Similarity	NPC186063
0.7841	Intermediate Similarity	NPC35627
0.7841	Intermediate Similarity	NPC476573
0.7841	Intermediate Similarity	NPC81247
0.7831	Intermediate Similarity	NPC294249
0.7829	Intermediate Similarity	NPC1229
0.7829	Intermediate Similarity	NPC59567
0.7811	Intermediate Similarity	NPC60538
0.7811	Intermediate Similarity	NPC207824
0.7805	Intermediate Similarity	NPC314682
0.7802	Intermediate Similarity	NPC298339
0.7797	Intermediate Similarity	NPC298979
0.7784	Intermediate Similarity	NPC24465
0.7778	Intermediate Similarity	NPC128560
0.7778	Intermediate Similarity	NPC199465
0.7778	Intermediate Similarity	NPC229166
0.7771	Intermediate Similarity	NPC60186
0.7765	Intermediate Similarity	NPC239775
0.7765	Intermediate Similarity	NPC223125
0.7758	Intermediate Similarity	NPC188163
0.7758	Intermediate Similarity	NPC328750
0.7758	Intermediate Similarity	NPC213206
0.7758	Intermediate Similarity	NPC474915
0.774	Intermediate Similarity	NPC13916
0.774	Intermediate Similarity	NPC264850
0.7719	Intermediate Similarity	NPC81733
0.7719	Intermediate Similarity	NPC326316
0.7714	Intermediate Similarity	NPC97072
0.7714	Intermediate Similarity	NPC18402
0.7714	Intermediate Similarity	NPC215829
0.7709	Intermediate Similarity	NPC168753
0.7709	Intermediate Similarity	NPC118274
0.7709	Intermediate Similarity	NPC69712
0.7709	Intermediate Similarity	NPC26240
0.7709	Intermediate Similarity	NPC477562
0.7701	Intermediate Similarity	NPC475326
0.7697	Intermediate Similarity	NPC210140
0.7692	Intermediate Similarity	NPC476144
0.7692	Intermediate Similarity	NPC106295
0.7692	Intermediate Similarity	NPC51957
0.7692	Intermediate Similarity	NPC16107
0.7692	Intermediate Similarity	NPC320223
0.7692	Intermediate Similarity	NPC210437
0.7692	Intermediate Similarity	NPC114364
0.7679	Intermediate Similarity	NPC130926
0.7674	Intermediate Similarity	NPC26601
0.7674	Intermediate Similarity	NPC476580
0.7665	Intermediate Similarity	NPC128019
0.7665	Intermediate Similarity	NPC136860
0.7665	Intermediate Similarity	NPC476567
0.7663	Intermediate Similarity	NPC116284
0.7657	Intermediate Similarity	NPC106786
0.7654	Intermediate Similarity	NPC204908
0.7654	Intermediate Similarity	NPC83198
0.7647	Intermediate Similarity	NPC7467
0.7644	Intermediate Similarity	NPC207239
0.7627	Intermediate Similarity	NPC476569
0.7624	Intermediate Similarity	NPC192135
0.7624	Intermediate Similarity	NPC66341
0.7624	Intermediate Similarity	NPC477020
0.7586	Intermediate Similarity	NPC99659
0.7586	Intermediate Similarity	NPC78733
0.7586	Intermediate Similarity	NPC325871
0.7584	Intermediate Similarity	NPC4138
0.7584	Intermediate Similarity	NPC284183
0.7584	Intermediate Similarity	NPC134858
0.7584	Intermediate Similarity	NPC121275
0.7578	Intermediate Similarity	NPC160193
0.7572	Intermediate Similarity	NPC470924
0.7557	Intermediate Similarity	NPC59028
0.7557	Intermediate Similarity	NPC92191
0.7544	Intermediate Similarity	NPC475959
0.7543	Intermediate Similarity	NPC57512
0.7543	Intermediate Similarity	NPC323443
0.7543	Intermediate Similarity	NPC180756
0.7542	Intermediate Similarity	NPC42549
0.7542	Intermediate Similarity	NPC317272
0.7542	Intermediate Similarity	NPC268503
0.7542	Intermediate Similarity	NPC240841
0.7542	Intermediate Similarity	NPC256012
0.7542	Intermediate Similarity	NPC250846
0.7541	Intermediate Similarity	NPC237044
0.753	Intermediate Similarity	NPC231572
0.7528	Intermediate Similarity	NPC233650
0.7527	Intermediate Similarity	NPC152680
0.7527	Intermediate Similarity	NPC190783
0.7527	Intermediate Similarity	NPC232386
0.7514	Intermediate Similarity	NPC477559
0.7514	Intermediate Similarity	NPC160298
0.7514	Intermediate Similarity	NPC135006
0.7514	Intermediate Similarity	NPC155442
0.7514	Intermediate Similarity	NPC266753
0.7514	Intermediate Similarity	NPC232924
0.7514	Intermediate Similarity	NPC477561
0.7514	Intermediate Similarity	NPC312918
0.7514	Intermediate Similarity	NPC476574
0.7514	Intermediate Similarity	NPC306902
0.75	Intermediate Similarity	NPC476572
0.75	Intermediate Similarity	NPC40389
0.75	Intermediate Similarity	NPC190332
0.75	Intermediate Similarity	NPC219162
0.75	Intermediate Similarity	NPC148014
0.75	Intermediate Similarity	NPC181653
0.75	Intermediate Similarity	NPC100566
0.75	Intermediate Similarity	NPC78359
0.75	Intermediate Similarity	NPC474325
0.75	Intermediate Similarity	NPC315707
0.75	Intermediate Similarity	NPC65490
0.7486	Intermediate Similarity	NPC41178
0.7486	Intermediate Similarity	NPC138487
0.7486	Intermediate Similarity	NPC304675
0.7486	Intermediate Similarity	NPC216459
0.7473	Intermediate Similarity	NPC477640

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 NPC21885 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	773
0.2-0.3	1079
0.3-0.4	2475
0.4-0.5	2652
0.5-0.6	1551
0.6-0.7	368
0.7-0.8	45
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9506	High Similarity	NPD2898	Approved
0.8046	Intermediate Similarity	NPD4010	Discontinued
0.7802	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD2489	Approved
0.7753	Intermediate Similarity	NPD27	Approved
0.7714	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7833	Phase 2
0.7714	Intermediate Similarity	NPD7831	Phase 2
0.7706	Intermediate Similarity	NPD3640	Phase 3
0.7706	Intermediate Similarity	NPD3639	Approved
0.7706	Intermediate Similarity	NPD3641	Approved
0.7692	Intermediate Similarity	NPD4584	Approved
0.7598	Intermediate Similarity	NPD2969	Approved
0.7598	Intermediate Similarity	NPD2970	Approved
0.7578	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6071	Discontinued
0.7529	Intermediate Similarity	NPD4772	Phase 2
0.7529	Intermediate Similarity	NPD4773	Phase 2
0.75	Intermediate Similarity	NPD5978	Approved
0.75	Intermediate Similarity	NPD5977	Approved
0.75	Intermediate Similarity	NPD2560	Approved
0.75	Intermediate Similarity	NPD2563	Approved
0.7485	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3051	Approved
0.7427	Intermediate Similarity	NPD2421	Approved
0.7427	Intermediate Similarity	NPD2420	Approved
0.7368	Intermediate Similarity	NPD2488	Approved
0.7368	Intermediate Similarity	NPD2490	Approved
0.7326	Intermediate Similarity	NPD7311	Approved
0.7326	Intermediate Similarity	NPD7310	Approved
0.7326	Intermediate Similarity	NPD7312	Approved
0.7326	Intermediate Similarity	NPD7313	Approved
0.7314	Intermediate Similarity	NPD4017	Approved
0.7287	Intermediate Similarity	NPD8054	Approved
0.7287	Intermediate Similarity	NPD8053	Approved
0.7287	Intermediate Similarity	NPD7309	Approved
0.7268	Intermediate Similarity	NPD4481	Phase 3
0.7263	Intermediate Similarity	NPD7906	Approved
0.7238	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4577	Approved
0.7234	Intermediate Similarity	NPD4578	Approved
0.7213	Intermediate Similarity	NPD6687	Approved
0.7213	Intermediate Similarity	NPD6688	Approved
0.7209	Intermediate Similarity	NPD5241	Discontinued
0.7191	Intermediate Similarity	NPD7298	Approved
0.7188	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3448	Approved
0.7172	Intermediate Similarity	NPD2491	Approved
0.7168	Intermediate Similarity	NPD3845	Phase 1
0.7158	Intermediate Similarity	NPD4166	Phase 2
0.712	Intermediate Similarity	NPD4663	Approved
0.7119	Intermediate Similarity	NPD824	Approved
0.7104	Intermediate Similarity	NPD6107	Approved
0.7085	Intermediate Similarity	NPD3057	Approved
0.7066	Intermediate Similarity	NPD2674	Phase 3
0.7056	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2493	Approved
0.7035	Intermediate Similarity	NPD3452	Approved
0.7035	Intermediate Similarity	NPD2494	Approved
0.7035	Intermediate Similarity	NPD3450	Approved
0.7006	Intermediate Similarity	NPD6031	Approved
0.7006	Intermediate Similarity	NPD6030	Approved
0.7	Intermediate Similarity	NPD3533	Approved
0.7	Intermediate Similarity	NPD2972	Approved
0.6984	Remote Similarity	NPD6297	Approved
0.6971	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2971	Approved
0.6963	Remote Similarity	NPD2968	Approved
0.6959	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4583	Approved
0.6931	Remote Similarity	NPD4582	Approved
0.6919	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD8099	Discontinued
0.6915	Remote Similarity	NPD8252	Approved
0.6915	Remote Similarity	NPD8251	Approved
0.6914	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5718	Phase 2
0.6905	Remote Similarity	NPD3144	Approved
0.6905	Remote Similarity	NPD3145	Approved
0.6897	Remote Similarity	NPD5177	Phase 3
0.6893	Remote Similarity	NPD3645	Discontinued
0.6885	Remote Similarity	NPD6788	Approved
0.6881	Remote Similarity	NPD4002	Approved
0.6881	Remote Similarity	NPD4004	Approved
0.6878	Remote Similarity	NPD5312	Approved
0.6878	Remote Similarity	NPD5313	Approved
0.6878	Remote Similarity	NPD8156	Discontinued
0.6868	Remote Similarity	NPD4585	Approved
0.6851	Remote Similarity	NPD5090	Approved
0.6851	Remote Similarity	NPD5089	Approved
0.6847	Remote Similarity	NPD4040	Phase 1
0.6842	Remote Similarity	NPD7047	Phase 3
0.6839	Remote Similarity	NPD6851	Approved
0.6839	Remote Similarity	NPD6853	Approved
0.6837	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD3124	Discontinued
0.6834	Remote Similarity	NPD2975	Approved
0.6834	Remote Similarity	NPD2974	Approved
0.6834	Remote Similarity	NPD2973	Approved
0.6824	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3620	Phase 2
0.6824	Remote Similarity	NPD3110	Approved
0.6824	Remote Similarity	NPD3109	Approved
0.6808	Remote Similarity	NPD6997	Phase 2
0.6802	Remote Similarity	NPD6896	Approved
0.6802	Remote Similarity	NPD6895	Approved
0.6793	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD1753	Discontinued
0.6761	Remote Similarity	NPD7907	Approved
0.676	Remote Similarity	NPD6090	Discontinued
0.6755	Remote Similarity	NPD2388	Discontinued
0.6744	Remote Similarity	NPD2492	Phase 1
0.6735	Remote Similarity	NPD7291	Discontinued
0.6733	Remote Similarity	NPD4107	Approved
0.6733	Remote Similarity	NPD4580	Approved
0.6731	Remote Similarity	NPD5676	Approved
0.6726	Remote Similarity	NPD3636	Approved
0.6726	Remote Similarity	NPD3637	Approved
0.6726	Remote Similarity	NPD3635	Approved
0.6723	Remote Similarity	NPD3692	Discontinued
0.672	Remote Similarity	NPD6894	Phase 1
0.6716	Remote Similarity	NPD4420	Approved
0.6704	Remote Similarity	NPD1424	Approved
0.6703	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2978	Approved
0.6685	Remote Similarity	NPD2120	Phase 2
0.6685	Remote Similarity	NPD2977	Approved
0.6684	Remote Similarity	NPD2904	Discontinued
0.6683	Remote Similarity	NPD8095	Phase 1
0.6667	Remote Similarity	NPD6873	Phase 2
0.6667	Remote Similarity	NPD4111	Phase 1
0.6667	Remote Similarity	NPD6331	Phase 2
0.6667	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5564	Approved
0.6667	Remote Similarity	NPD4665	Approved
0.665	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7802	Discontinued
0.6634	Remote Similarity	NPD7497	Discontinued
0.663	Remote Similarity	NPD1914	Approved
0.6618	Remote Similarity	NPD4482	Phase 3
0.6615	Remote Similarity	NPD4873	Discontinued
0.6615	Remote Similarity	NPD7280	Phase 3
0.6615	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7281	Phase 3
0.6615	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3060	Approved
0.6597	Remote Similarity	NPD3446	Phase 1
0.6596	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4666	Phase 3
0.6592	Remote Similarity	NPD7048	Phase 3
0.6592	Remote Similarity	NPD6667	Approved
0.6592	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6666	Approved
0.6588	Remote Similarity	NPD3595	Approved
0.6588	Remote Similarity	NPD2606	Approved
0.6588	Remote Similarity	NPD3594	Approved
0.6588	Remote Similarity	NPD2605	Approved
0.6585	Remote Similarity	NPD5005	Approved
0.6585	Remote Similarity	NPD5006	Approved
0.6582	Remote Similarity	NPD6618	Phase 2
0.6578	Remote Similarity	NPD4055	Discovery
0.6576	Remote Similarity	NPD7110	Phase 1
0.6576	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD5754	Discontinued
0.657	Remote Similarity	NPD4475	Approved
0.657	Remote Similarity	NPD4474	Approved
0.6557	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2157	Approved
0.655	Remote Similarity	NPD5156	Approved
0.655	Remote Similarity	NPD5155	Approved
0.6548	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5709	Phase 3
0.6534	Remote Similarity	NPD2161	Phase 2
0.6533	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6042	Phase 2
0.6528	Remote Similarity	NPD42	Phase 2
0.6527	Remote Similarity	NPD2232	Approved
0.6527	Remote Similarity	NPD2233	Approved
0.6527	Remote Similarity	NPD2230	Approved
0.6519	Remote Similarity	NPD7019	Approved
0.6519	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7020	Approved
0.6517	Remote Similarity	NPD4237	Approved
0.6517	Remote Similarity	NPD3638	Discontinued
0.6517	Remote Similarity	NPD4236	Phase 3
0.6509	Remote Similarity	NPD3053	Approved
0.6509	Remote Similarity	NPD3055	Approved
0.6506	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5772	Approved
0.6505	Remote Similarity	NPD5773	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