NPASS Compound

Structure

NPC471124 OpenBabel07101718292D 24 28 0 0 1 0 0 0 0 0999 V2000 1.2024 0.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6146 -0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0741 -0.5292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0435 -0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1230 -0.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2822 -0.3885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2820 0.4489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0976 -0.2193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3799 -0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.5388 1.1180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0922 -0.3238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3479 2.7058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 2.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 17 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 21 1 0 0 0 0 15 21 1 0 0 0 0 15 22 2 0 0 0 0 16 20 1 0 0 0 0 16 23 2 0 0 0 0 17 19 1 1 0 0 0 18 19 1 6 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.16
Volume:	329.58
LogP:	1.775
LogD:	1.802
LogS:	-4.348
# Rotatable Bonds:	1
TPSA:	60.85
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.86
Synthetic Accessibility Score:	4.778
Fsp3:	0.579
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:	-4.969
MDCK Permeability:	2.787667472148314e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	48.01375961303711%
Volume Distribution (VD):	0.798
Pgp-substrate:	55.663333892822266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.41
CYP2C19-inhibitor:	0.533
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.791
CYP2C9-substrate:	0.518
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.939

ADMET: Excretion

Clearance (CL):	5.6
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.43
Drug-inuced Liver Injury (DILI):	0.147
AMES Toxicity:	0.13
Rat Oral Acute Toxicity:	0.539
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.401
Carcinogencity:	0.974
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.094

Download Data

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

Natural Product: NPC471124

Natural Product ID:	NPC471124
*Common Name:**	LZUIMMLDZPLMRH-PWCSWUJKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LZUIMMLDZPLMRH-PWCSWUJKSA-N
Standard InCHI:	InChI=1S/C19H22N2O3/c1-2-17-9-5-11-20-16(23)12-18(24)13-6-3-4-7-14(13)21(19(17,18)20)15(22)8-10-17/h3-4,6-7,24H,2,5,8-12H2,1H3/t17-,18-,19?/m1/s1
SMILES:	CC[C@@]12CCCN3C42N(C(=O)CC1)c1c([C@]4(O)CC3=O)cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375648
PubChem CID:	71714599
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002758] Rhazinilam 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
NPO10199	Leuconotis griffithii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20153644]
NPO10199	Leuconotis griffithii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23647487]
NPO10199	Leuconotis griffithii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[30362746]
NPO10199	Leuconotis griffithii	n.a.	n.a.	n.a.	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	12.0	ug.mL-1	PMID[448199]

☑ 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 NPC471124 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	272
0.1-0.2	1171
0.2-0.3	4990
0.3-0.4	17266
0.4-0.5	14254
0.5-0.6	4002
0.6-0.7	633
0.7-0.8	102
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC471122
0.8889	High Similarity	NPC470548
0.8344	Intermediate Similarity	NPC471123
0.8117	Intermediate Similarity	NPC469560
0.7952	Intermediate Similarity	NPC476231
0.788	Intermediate Similarity	NPC471436
0.7845	Intermediate Similarity	NPC472539
0.7845	Intermediate Similarity	NPC470787
0.7845	Intermediate Similarity	NPC472540
0.7811	Intermediate Similarity	NPC472114
0.7811	Intermediate Similarity	NPC472115
0.7802	Intermediate Similarity	NPC472542
0.7802	Intermediate Similarity	NPC472541
0.7771	Intermediate Similarity	NPC113946
0.7738	Intermediate Similarity	NPC472101
0.7738	Intermediate Similarity	NPC472120
0.7738	Intermediate Similarity	NPC472117
0.7647	Intermediate Similarity	NPC472106
0.7622	Intermediate Similarity	NPC473329
0.761	Intermediate Similarity	NPC315051
0.7576	Intermediate Similarity	NPC66936
0.7553	Intermediate Similarity	NPC477179
0.7543	Intermediate Similarity	NPC475607
0.7529	Intermediate Similarity	NPC139085
0.7529	Intermediate Similarity	NPC251212
0.7529	Intermediate Similarity	NPC214626
0.7529	Intermediate Similarity	NPC285622
0.7513	Intermediate Similarity	NPC477178
0.7513	Intermediate Similarity	NPC254850
0.7513	Intermediate Similarity	NPC477180
0.7513	Intermediate Similarity	NPC477181
0.75	Intermediate Similarity	NPC474081
0.75	Intermediate Similarity	NPC29285
0.7486	Intermediate Similarity	NPC475594
0.7474	Intermediate Similarity	NPC477173
0.7474	Intermediate Similarity	NPC477174
0.7474	Intermediate Similarity	NPC470490
0.7473	Intermediate Similarity	NPC105055
0.7473	Intermediate Similarity	NPC473569
0.7473	Intermediate Similarity	NPC22689
0.7471	Intermediate Similarity	NPC68650
0.7471	Intermediate Similarity	NPC309531
0.7471	Intermediate Similarity	NPC472102
0.7471	Intermediate Similarity	NPC355
0.7458	Intermediate Similarity	NPC475761
0.7453	Intermediate Similarity	NPC470301
0.7444	Intermediate Similarity	NPC259626
0.7435	Intermediate Similarity	NPC470488
0.7412	Intermediate Similarity	NPC36495
0.7396	Intermediate Similarity	NPC471945
0.7396	Intermediate Similarity	NPC471950
0.7396	Intermediate Similarity	NPC475259
0.7396	Intermediate Similarity	NPC470491
0.7389	Intermediate Similarity	NPC2933
0.7384	Intermediate Similarity	NPC313757
0.7377	Intermediate Similarity	NPC128582
0.736	Intermediate Similarity	NPC474041
0.7358	Intermediate Similarity	NPC471946
0.7358	Intermediate Similarity	NPC471951
0.7356	Intermediate Similarity	NPC33507
0.7353	Intermediate Similarity	NPC222029
0.7345	Intermediate Similarity	NPC129624
0.7333	Intermediate Similarity	NPC256288
0.733	Intermediate Similarity	NPC470489
0.732	Intermediate Similarity	NPC191817
0.732	Intermediate Similarity	NPC475359
0.731	Intermediate Similarity	NPC276085
0.7303	Intermediate Similarity	NPC260075
0.7299	Intermediate Similarity	NPC214960
0.7299	Intermediate Similarity	NPC279527
0.7277	Intermediate Similarity	NPC295548
0.7262	Intermediate Similarity	NPC154602
0.7247	Intermediate Similarity	NPC476441
0.7239	Intermediate Similarity	NPC22082
0.7239	Intermediate Similarity	NPC186284
0.7238	Intermediate Similarity	NPC477159
0.7232	Intermediate Similarity	NPC96901
0.7225	Intermediate Similarity	NPC176983
0.7225	Intermediate Similarity	NPC286871
0.7222	Intermediate Similarity	NPC166169
0.7216	Intermediate Similarity	NPC469915
0.7213	Intermediate Similarity	NPC473615
0.7208	Intermediate Similarity	NPC471663
0.7202	Intermediate Similarity	NPC225400
0.7174	Intermediate Similarity	NPC229484
0.7165	Intermediate Similarity	NPC471155
0.7165	Intermediate Similarity	NPC472538
0.7165	Intermediate Similarity	NPC470786
0.7164	Intermediate Similarity	NPC272174
0.7151	Intermediate Similarity	NPC469428
0.7143	Intermediate Similarity	NPC109787
0.7135	Intermediate Similarity	NPC242269
0.7135	Intermediate Similarity	NPC292675
0.7129	Intermediate Similarity	NPC474896
0.7128	Intermediate Similarity	NPC270241
0.7126	Intermediate Similarity	NPC85651
0.712	Intermediate Similarity	NPC67904
0.712	Intermediate Similarity	NPC138830
0.7101	Intermediate Similarity	NPC318086
0.7094	Intermediate Similarity	NPC31097
0.7081	Intermediate Similarity	NPC473815
0.7076	Intermediate Similarity	NPC478076
0.7069	Intermediate Similarity	NPC225319
0.7052	Intermediate Similarity	NPC61013
0.7048	Intermediate Similarity	NPC308197
0.7039	Intermediate Similarity	NPC476425
0.703	Intermediate Similarity	NPC219397
0.7018	Intermediate Similarity	NPC285381
0.7011	Intermediate Similarity	NPC193410
0.6994	Remote Similarity	NPC267508
0.6978	Remote Similarity	NPC99043
0.6978	Remote Similarity	NPC218594
0.6973	Remote Similarity	NPC307396
0.6971	Remote Similarity	NPC248117
0.6971	Remote Similarity	NPC315368
0.6971	Remote Similarity	NPC143457
0.6954	Remote Similarity	NPC153694
0.6954	Remote Similarity	NPC211525
0.6954	Remote Similarity	NPC104345
0.695	Remote Similarity	NPC473006
0.6947	Remote Similarity	NPC221687
0.6944	Remote Similarity	NPC177261
0.6941	Remote Similarity	NPC242000
0.694	Remote Similarity	NPC39822
0.6931	Remote Similarity	NPC473004
0.6927	Remote Similarity	NPC472118
0.6927	Remote Similarity	NPC100863
0.6919	Remote Similarity	NPC302235
0.691	Remote Similarity	NPC278887
0.6902	Remote Similarity	NPC476428
0.6895	Remote Similarity	NPC470485
0.6885	Remote Similarity	NPC321211
0.6882	Remote Similarity	NPC254798
0.6882	Remote Similarity	NPC322621
0.6878	Remote Similarity	NPC203628
0.6878	Remote Similarity	NPC276430
0.6875	Remote Similarity	NPC201424
0.6875	Remote Similarity	NPC162440
0.6872	Remote Similarity	NPC167724
0.6872	Remote Similarity	NPC223595
0.6872	Remote Similarity	NPC224970
0.6869	Remote Similarity	NPC285192
0.6862	Remote Similarity	NPC284706
0.686	Remote Similarity	NPC243756
0.6857	Remote Similarity	NPC123241
0.6845	Remote Similarity	NPC478077
0.6842	Remote Similarity	NPC204970
0.6836	Remote Similarity	NPC99632
0.6836	Remote Similarity	NPC293458
0.6836	Remote Similarity	NPC282339
0.6825	Remote Similarity	NPC5630
0.6823	Remote Similarity	NPC97100
0.6823	Remote Similarity	NPC473375
0.6818	Remote Similarity	NPC263709
0.6818	Remote Similarity	NPC97380
0.6818	Remote Similarity	NPC243673
0.6818	Remote Similarity	NPC310403
0.6818	Remote Similarity	NPC63210
0.6818	Remote Similarity	NPC148468
0.6802	Remote Similarity	NPC329833
0.6791	Remote Similarity	NPC473007
0.679	Remote Similarity	NPC231382
0.6789	Remote Similarity	NPC470483
0.6788	Remote Similarity	NPC90967
0.6788	Remote Similarity	NPC471199
0.6784	Remote Similarity	NPC212799
0.678	Remote Similarity	NPC474058
0.6776	Remote Similarity	NPC203202
0.6776	Remote Similarity	NPC264482
0.6774	Remote Similarity	NPC159963
0.6769	Remote Similarity	NPC475489
0.6766	Remote Similarity	NPC472243
0.6766	Remote Similarity	NPC130251
0.676	Remote Similarity	NPC52059
0.676	Remote Similarity	NPC470069
0.6757	Remote Similarity	NPC286994
0.6757	Remote Similarity	NPC11149
0.6753	Remote Similarity	NPC132874
0.6753	Remote Similarity	NPC265642
0.6753	Remote Similarity	NPC138615
0.6753	Remote Similarity	NPC218733
0.675	Remote Similarity	NPC477160
0.6742	Remote Similarity	NPC315498
0.6742	Remote Similarity	NPC230942
0.6742	Remote Similarity	NPC472121
0.6739	Remote Similarity	NPC476326
0.6738	Remote Similarity	NPC97584
0.6738	Remote Similarity	NPC245741
0.6737	Remote Similarity	NPC473298
0.6736	Remote Similarity	NPC303214
0.6735	Remote Similarity	NPC471512
0.6732	Remote Similarity	NPC248601
0.673	Remote Similarity	NPC477175
0.673	Remote Similarity	NPC470730
0.672	Remote Similarity	NPC21425
0.672	Remote Similarity	NPC475962
0.6718	Remote Similarity	NPC106118
0.6703	Remote Similarity	NPC6974
0.6702	Remote Similarity	NPC52262
0.6702	Remote Similarity	NPC25401

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 NPC471124 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	484
0.2-0.3	673
0.3-0.4	1245
0.4-0.5	3263
0.5-0.6	2903
0.6-0.7	405
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7456	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4430	Phase 2
0.7255	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2791	Discontinued
0.7239	Intermediate Similarity	NPD3625	Discontinued
0.7229	Intermediate Similarity	NPD3141	Discontinued
0.7081	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7735	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2820	Phase 3
0.7033	Intermediate Similarity	NPD6878	Phase 2
0.7033	Intermediate Similarity	NPD6879	Phase 2
0.7019	Intermediate Similarity	NPD7086	Phase 2
0.7017	Intermediate Similarity	NPD5600	Discontinued
0.6988	Remote Similarity	NPD2365	Approved
0.6923	Remote Similarity	NPD3449	Discontinued
0.6914	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8240	Discontinued
0.6813	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1663	Discontinued
0.6792	Remote Similarity	NPD6320	Approved
0.6791	Remote Similarity	NPD6557	Phase 2
0.6786	Remote Similarity	NPD6566	Discontinued
0.6782	Remote Similarity	NPD4120	Approved
0.6782	Remote Similarity	NPD4121	Phase 3
0.6778	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3983	Phase 3
0.6772	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6017	Discontinued
0.6763	Remote Similarity	NPD3277	Phase 3
0.676	Remote Similarity	NPD4796	Discontinued
0.6743	Remote Similarity	NPD5743	Approved
0.6743	Remote Similarity	NPD5741	Approved
0.6743	Remote Similarity	NPD5742	Approved
0.6742	Remote Similarity	NPD1742	Approved
0.6742	Remote Similarity	NPD1743	Approved
0.6742	Remote Similarity	NPD19	Approved
0.6723	Remote Similarity	NPD7599	Phase 2
0.6706	Remote Similarity	NPD5918	Discontinued
0.6705	Remote Similarity	NPD6395	Phase 2
0.6705	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD3790	Phase 2
0.6687	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5639	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5997	Discontinued
0.6647	Remote Similarity	NPD5024	Approved
0.6615	Remote Similarity	NPD5042	Phase 1
0.6609	Remote Similarity	NPD5748	Phase 2
0.6597	Remote Similarity	NPD8025	Phase 2
0.6593	Remote Similarity	NPD6457	Approved
0.6592	Remote Similarity	NPD7600	Phase 2
0.6591	Remote Similarity	NPD5086	Approved
0.6582	Remote Similarity	NPD5856	Discontinued
0.6578	Remote Similarity	NPD3227	Phase 2
0.6566	Remote Similarity	NPD5184	Approved
0.6566	Remote Similarity	NPD5185	Approved
0.6566	Remote Similarity	NPD5182	Approved
0.6558	Remote Similarity	NPD5179	Approved
0.6558	Remote Similarity	NPD5181	Approved
0.6558	Remote Similarity	NPD5180	Approved
0.6552	Remote Similarity	NPD4682	Phase 2
0.6548	Remote Similarity	NPD7231	Approved
0.6548	Remote Similarity	NPD7230	Approved
0.6548	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6999	Discontinued
0.6545	Remote Similarity	NPD6484	Approved
0.6545	Remote Similarity	NPD6483	Approved
0.6538	Remote Similarity	NPD1344	Phase 2
0.6536	Remote Similarity	NPD33	Approved
0.6536	Remote Similarity	NPD4393	Approved
0.6532	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD1271	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5993	Phase 1
0.65	Remote Similarity	NPD4311	Approved
0.65	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6665	Discontinued
0.6474	Remote Similarity	NPD5933	Phase 3
0.6474	Remote Similarity	NPD5923	Phase 1
0.6474	Remote Similarity	NPD5932	Phase 3
0.6474	Remote Similarity	NPD5931	Phase 3
0.6467	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6310	Approved
0.6467	Remote Similarity	NPD6309	Approved
0.6467	Remote Similarity	NPD6311	Approved
0.6457	Remote Similarity	NPD5942	Approved
0.6457	Remote Similarity	NPD5941	Approved
0.6457	Remote Similarity	NPD4888	Discontinued
0.6457	Remote Similarity	NPD4432	Discontinued
0.6456	Remote Similarity	NPD998	Approved
0.6455	Remote Similarity	NPD3990	Phase 3
0.6453	Remote Similarity	NPD7665	Phase 2
0.6453	Remote Similarity	NPD7082	Approved
0.6453	Remote Similarity	NPD6301	Phase 2
0.6453	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7666	Phase 3
0.6448	Remote Similarity	NPD5823	Approved
0.6443	Remote Similarity	NPD2327	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3240	Phase 2
0.644	Remote Similarity	NPD8167	Discontinued
0.6436	Remote Similarity	NPD7001	Phase 3
0.6433	Remote Similarity	NPD2093	Discontinued
0.6432	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4334	Discontinued
0.6425	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD7259	Approved
0.6413	Remote Similarity	NPD7126	Discontinued
0.6412	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7570	Approved
0.641	Remote Similarity	NPD7569	Approved
0.6409	Remote Similarity	NPD2506	Approved
0.6409	Remote Similarity	NPD2511	Approved
0.6406	Remote Similarity	NPD3315	Phase 3
0.6402	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6259	Discontinued
0.6402	Remote Similarity	NPD3989	Phase 3
0.64	Remote Similarity	NPD5552	Discontinued
0.64	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD3439	Approved
0.6389	Remote Similarity	NPD8060	Phase 1
0.6389	Remote Similarity	NPD8630	Approved
0.6383	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4317	Approved
0.6381	Remote Similarity	NPD7168	Phase 3
0.638	Remote Similarity	NPD6792	Phase 3
0.6379	Remote Similarity	NPD7295	Approved
0.6378	Remote Similarity	NPD5183	Approved
0.6378	Remote Similarity	NPD5186	Approved
0.6374	Remote Similarity	NPD3391	Approved
0.6373	Remote Similarity	NPD6891	Phase 2
0.6364	Remote Similarity	NPD4161	Discontinued
0.6359	Remote Similarity	NPD6659	Phase 2
0.6359	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1625	Approved
0.6354	Remote Similarity	NPD5255	Approved
0.6354	Remote Similarity	NPD4485	Approved
0.6354	Remote Similarity	NPD4514	Approved
0.6353	Remote Similarity	NPD6358	Phase 2
0.6353	Remote Similarity	NPD6636	Phase 3
0.6349	Remote Similarity	NPD5774	Approved
0.6349	Remote Similarity	NPD5775	Approved
0.6348	Remote Similarity	NPD8402	Approved
0.6348	Remote Similarity	NPD8400	Approved
0.6348	Remote Similarity	NPD3248	Phase 1
0.6348	Remote Similarity	NPD8401	Approved
0.6345	Remote Similarity	NPD4602	Approved
0.6344	Remote Similarity	NPD3824	Phase 1
0.634	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4152	Approved
0.6337	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5214	Phase 2
0.6327	Remote Similarity	NPD6887	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5131	Approved
0.6322	Remote Similarity	NPD7487	Discontinued
0.6319	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD5582	Discontinued
0.6313	Remote Similarity	NPD2790	Discontinued
0.631	Remote Similarity	NPD1527	Phase 2
0.631	Remote Similarity	NPD1595	Approved
0.631	Remote Similarity	NPD1594	Phase 3
0.6308	Remote Similarity	NPD3321	Discontinued
0.6307	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD6768	Approved
0.6299	Remote Similarity	NPD4116	Approved
0.6298	Remote Similarity	NPD7011	Discontinued
0.6296	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4092	Approved
0.6294	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5990	Approved
0.6289	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4515	Suspended
0.6289	Remote Similarity	NPD5991	Approved
0.6286	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD2813	Phase 3
0.628	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.628	Remote Similarity	NPD3080	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD3422	Phase 3
0.6277	Remote Similarity	NPD3423	Phase 2
0.6277	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD7200	Approved
0.6271	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD2622	Approved
0.6265	Remote Similarity	NPD4549	Discontinued
0.6264	Remote Similarity	NPD2427	Approved
0.6264	Remote Similarity	NPD6060	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