NPASS Compound

Structure

NPC469558 OpenBabel07101718332D 36 38 0 0 1 0 0 0 0 0999 V2000 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 6 16 1 0 0 0 0 7 26 1 0 0 0 0 8 26 1 0 0 0 0 10 13 2 0 0 0 0 11 14 2 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 16 28 2 0 0 0 0 16 32 1 0 0 0 0 17 33 1 0 0 0 0 18 26 1 0 0 0 0 18 35 1 0 0 0 0 19 15 1 6 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 20 32 1 1 0 0 0 21 23 1 0 0 0 0 21 34 1 6 0 0 0 22 27 1 0 0 0 0 22 29 2 0 0 0 0 23 27 1 1 0 0 0 23 36 1 0 0 0 0 24 30 2 0 0 0 0 24 33 1 0 0 0 0 25 31 2 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 9 1 1 0 0 0 27 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.24
Volume:	510.536
LogP:	2.296
LogD:	1.687
LogS:	-3.629
# Rotatable Bonds:	12
TPSA:	121.03
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.153
Synthetic Accessibility Score:	5.268
Fsp3:	0.63
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.849
MDCK Permeability:	4.5851353206671774e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.183
20% Bioavailability (F20%):	0.674
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.684
Plasma Protein Binding (PPB):	71.08570098876953%
Volume Distribution (VD):	2.608
Pgp-substrate:	20.027257919311523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.154
CYP2C19-inhibitor:	0.243
CYP2C19-substrate:	0.766
CYP2C9-inhibitor:	0.591
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.653

ADMET: Excretion

Clearance (CL):	10.287
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.864
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.603
Maximum Recommended Daily Dose:	0.326
Skin Sensitization:	0.245
Carcinogencity:	0.132
Eye Corrosion:	0.917
Eye Irritation:	0.213
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC469558

Natural Product ID:	NPC469558
*Common Name:**	Altaicalarin D
IUPAC Name:	[(1S,2S,3R,4S,6S)-4-acetyloxy-3-[4-(3,3-dimethyloxiran-2-yl)-3-[(Z)-2-methylbut-2-enoyl]oxybut-1-en-2-yl]-6-methyl-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl] (Z)-2-methylbut-2-enoate
Synonyms:	altaicalarin D
Standard InCHIKey:	VMZMBTIZKOPION-LAFIFDADSA-N
Standard InCHI:	InChI=1S/C27H36O9/c1-10-13(3)24(30)33-17(12-18-26(7,8)35-18)15(5)19-20(32-16(6)28)22(29)27(9)23(36-27)21(19)34-25(31)14(4)11-2/h10-11,17-21,23H,5,12H2,1-4,6-9H3/b13-10-,14-11-/t17?,18?,19-,20-,21-,23-,27+/m0/s1
SMILES:	CC=C(C)C(=O)OC1C(C(C(=O)C2(C1O2)C)OC(=O)C)C(=C)C(CC3C(O3)(C)C)OC(=O)C(=CC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087160
PubChem CID:	46186621
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO12711	Ligularia altaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20073490]
NPO12711	Ligularia altaica	Species	Asteraceae	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
EC50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[475029]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[475029]
NPT91	Cell Line	KB	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[475029]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	18.9	ug.mL-1	PMID[475029]

☑ 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 NPC469558 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	299
0.1-0.2	2164
0.2-0.3	5684
0.3-0.4	9035
0.4-0.5	15136
0.5-0.6	7542
0.6-0.7	2358
0.7-0.8	452
0.8-0.85	19
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC474716
0.9	High Similarity	NPC469551
0.8365	Intermediate Similarity	NPC264477
0.8365	Intermediate Similarity	NPC477511
0.8349	Intermediate Similarity	NPC194619
0.8333	Intermediate Similarity	NPC471934
0.8273	Intermediate Similarity	NPC471933
0.8265	Intermediate Similarity	NPC475087
0.8257	Intermediate Similarity	NPC473975
0.8257	Intermediate Similarity	NPC473594
0.8257	Intermediate Similarity	NPC474586
0.8257	Intermediate Similarity	NPC473843
0.8224	Intermediate Similarity	NPC470975
0.8224	Intermediate Similarity	NPC470979
0.8224	Intermediate Similarity	NPC103088
0.8214	Intermediate Similarity	NPC477509
0.8198	Intermediate Similarity	NPC33360
0.8198	Intermediate Similarity	NPC477126
0.819	Intermediate Similarity	NPC473802
0.8131	Intermediate Similarity	NPC471143
0.8131	Intermediate Similarity	NPC477127
0.8131	Intermediate Similarity	NPC477510
0.812	Intermediate Similarity	NPC473709
0.812	Intermediate Similarity	NPC473919
0.8095	Intermediate Similarity	NPC477512
0.8077	Intermediate Similarity	NPC471140
0.8058	Intermediate Similarity	NPC469583
0.8051	Intermediate Similarity	NPC471939
0.8034	Intermediate Similarity	NPC472399
0.8019	Intermediate Similarity	NPC201718
0.7983	Intermediate Similarity	NPC471940
0.7982	Intermediate Similarity	NPC477513
0.7982	Intermediate Similarity	NPC475587
0.7982	Intermediate Similarity	NPC296822
0.7982	Intermediate Similarity	NPC475510
0.7981	Intermediate Similarity	NPC472997
0.7981	Intermediate Similarity	NPC472996
0.7981	Intermediate Similarity	NPC17585
0.7946	Intermediate Similarity	NPC317687
0.7941	Intermediate Similarity	NPC20713
0.7928	Intermediate Similarity	NPC253906
0.7913	Intermediate Similarity	NPC240509
0.7909	Intermediate Similarity	NPC473595
0.7909	Intermediate Similarity	NPC473939
0.7905	Intermediate Similarity	NPC472998
0.7895	Intermediate Similarity	NPC474333
0.7863	Intermediate Similarity	NPC472401
0.7857	Intermediate Similarity	NPC317107
0.7857	Intermediate Similarity	NPC475495
0.7843	Intermediate Similarity	NPC475748
0.783	Intermediate Similarity	NPC264378
0.7797	Intermediate Similarity	NPC19464
0.7788	Intermediate Similarity	NPC477093
0.7788	Intermediate Similarity	NPC473522
0.7788	Intermediate Similarity	NPC475277
0.7788	Intermediate Similarity	NPC471147
0.7778	Intermediate Similarity	NPC471126
0.7778	Intermediate Similarity	NPC157252
0.7778	Intermediate Similarity	NPC471128
0.7778	Intermediate Similarity	NPC145182
0.7778	Intermediate Similarity	NPC39996
0.7769	Intermediate Similarity	NPC236999
0.7768	Intermediate Similarity	NPC281624
0.776	Intermediate Similarity	NPC68282
0.775	Intermediate Similarity	NPC470973
0.775	Intermediate Similarity	NPC225049
0.7748	Intermediate Similarity	NPC322903
0.7739	Intermediate Similarity	NPC476710
0.7739	Intermediate Similarity	NPC270478
0.7739	Intermediate Similarity	NPC476711
0.7736	Intermediate Similarity	NPC236176
0.7724	Intermediate Similarity	NPC476193
0.7724	Intermediate Similarity	NPC180902
0.7724	Intermediate Similarity	NPC475139
0.7719	Intermediate Similarity	NPC159333
0.7719	Intermediate Similarity	NPC470120
0.7712	Intermediate Similarity	NPC52839
0.7692	Intermediate Similarity	NPC472667
0.7692	Intermediate Similarity	NPC470186
0.7685	Intermediate Similarity	NPC474339
0.7685	Intermediate Similarity	NPC15993
0.7685	Intermediate Similarity	NPC164598
0.7679	Intermediate Similarity	NPC469370
0.7672	Intermediate Similarity	NPC476713
0.7672	Intermediate Similarity	NPC58662
0.7672	Intermediate Similarity	NPC476712
0.7667	Intermediate Similarity	NPC24651
0.7664	Intermediate Similarity	NPC471932
0.7664	Intermediate Similarity	NPC208233
0.7658	Intermediate Similarity	NPC266514
0.7658	Intermediate Similarity	NPC180744
0.7647	Intermediate Similarity	NPC475902
0.7647	Intermediate Similarity	NPC162009
0.7647	Intermediate Similarity	NPC257017
0.7642	Intermediate Similarity	NPC472995
0.7642	Intermediate Similarity	NPC35498
0.7642	Intermediate Similarity	NPC476275
0.7636	Intermediate Similarity	NPC474741
0.7632	Intermediate Similarity	NPC473877
0.7627	Intermediate Similarity	NPC4548
0.7623	Intermediate Similarity	NPC476859
0.7619	Intermediate Similarity	NPC66581
0.7615	Intermediate Similarity	NPC149371
0.7615	Intermediate Similarity	NPC320019
0.7615	Intermediate Similarity	NPC324017
0.7615	Intermediate Similarity	NPC471148
0.7607	Intermediate Similarity	NPC251310
0.7607	Intermediate Similarity	NPC472397
0.7607	Intermediate Similarity	NPC171905
0.7607	Intermediate Similarity	NPC472758
0.7607	Intermediate Similarity	NPC471125
0.7603	Intermediate Similarity	NPC217901
0.7603	Intermediate Similarity	NPC473635
0.76	Intermediate Similarity	NPC100017
0.76	Intermediate Similarity	NPC475154
0.76	Intermediate Similarity	NPC475500
0.76	Intermediate Similarity	NPC182266
0.76	Intermediate Similarity	NPC471137
0.76	Intermediate Similarity	NPC471136
0.76	Intermediate Similarity	NPC223356
0.76	Intermediate Similarity	NPC473548
0.7586	Intermediate Similarity	NPC190185
0.7586	Intermediate Similarity	NPC154363
0.7586	Intermediate Similarity	NPC213084
0.7586	Intermediate Similarity	NPC471127
0.7586	Intermediate Similarity	NPC470793
0.7586	Intermediate Similarity	NPC234858
0.7583	Intermediate Similarity	NPC67251
0.7583	Intermediate Similarity	NPC18945
0.7583	Intermediate Similarity	NPC265557
0.7583	Intermediate Similarity	NPC91693
0.7583	Intermediate Similarity	NPC105926
0.757	Intermediate Similarity	NPC474921
0.7565	Intermediate Similarity	NPC94509
0.7563	Intermediate Similarity	NPC310511
0.7563	Intermediate Similarity	NPC470779
0.7561	Intermediate Similarity	NPC162495
0.7549	Intermediate Similarity	NPC231889
0.7545	Intermediate Similarity	NPC472755
0.7545	Intermediate Similarity	NPC474166
0.7545	Intermediate Similarity	NPC19239
0.7542	Intermediate Similarity	NPC22628
0.7542	Intermediate Similarity	NPC255081
0.7542	Intermediate Similarity	NPC5991
0.7542	Intermediate Similarity	NPC475520
0.7542	Intermediate Similarity	NPC476107
0.7542	Intermediate Similarity	NPC275696
0.7542	Intermediate Similarity	NPC5989
0.7542	Intermediate Similarity	NPC471108
0.7541	Intermediate Similarity	NPC168849
0.7541	Intermediate Similarity	NPC475273
0.7525	Intermediate Similarity	NPC474547
0.7523	Intermediate Similarity	NPC47880
0.7523	Intermediate Similarity	NPC476478
0.7523	Intermediate Similarity	NPC476270
0.7521	Intermediate Similarity	NPC469684
0.7521	Intermediate Similarity	NPC10721
0.7521	Intermediate Similarity	NPC475305
0.7521	Intermediate Similarity	NPC145238
0.7521	Intermediate Similarity	NPC470922
0.7521	Intermediate Similarity	NPC476729
0.7521	Intermediate Similarity	NPC471146
0.7521	Intermediate Similarity	NPC470778
0.7521	Intermediate Similarity	NPC146432
0.75	Intermediate Similarity	NPC312833
0.75	Intermediate Similarity	NPC170538
0.75	Intermediate Similarity	NPC80650
0.75	Intermediate Similarity	NPC475606
0.75	Intermediate Similarity	NPC299849
0.75	Intermediate Similarity	NPC476852
0.75	Intermediate Similarity	NPC251564
0.75	Intermediate Similarity	NPC474213
0.75	Intermediate Similarity	NPC476855
0.75	Intermediate Similarity	NPC475314
0.75	Intermediate Similarity	NPC477189
0.75	Intermediate Similarity	NPC469718
0.75	Intermediate Similarity	NPC329857
0.748	Intermediate Similarity	NPC477713
0.748	Intermediate Similarity	NPC477712
0.7479	Intermediate Similarity	NPC143755
0.7479	Intermediate Similarity	NPC317635
0.7479	Intermediate Similarity	NPC329008
0.7478	Intermediate Similarity	NPC475391
0.7477	Intermediate Similarity	NPC76862
0.7477	Intermediate Similarity	NPC158416
0.7477	Intermediate Similarity	NPC118159
0.7477	Intermediate Similarity	NPC39859
0.7477	Intermediate Similarity	NPC470883
0.7477	Intermediate Similarity	NPC279722
0.7477	Intermediate Similarity	NPC476315
0.7459	Intermediate Similarity	NPC293112
0.7458	Intermediate Similarity	NPC124676
0.7458	Intermediate Similarity	NPC146280
0.7458	Intermediate Similarity	NPC475401
0.7458	Intermediate Similarity	NPC470420
0.7458	Intermediate Similarity	NPC473720
0.7456	Intermediate Similarity	NPC89408
0.7456	Intermediate Similarity	NPC100908
0.7455	Intermediate Similarity	NPC472754
0.7453	Intermediate Similarity	NPC473316

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 NPC469558 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	2632
0.2-0.3	3622
0.3-0.4	1734
0.4-0.5	589
0.5-0.6	230
0.6-0.7	29
0.7-0.8	7
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
0.7593	Intermediate Similarity	NPD6648	Approved
0.7523	Intermediate Similarity	NPD5344	Discontinued
0.75	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD46	Approved
0.717	Intermediate Similarity	NPD6698	Approved
0.7069	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6921	Approved
0.6803	Remote Similarity	NPD7115	Discovery
0.6774	Remote Similarity	NPD6319	Approved
0.6723	Remote Similarity	NPD6371	Approved
0.6697	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD6008	Approved
0.6636	Remote Similarity	NPD7983	Approved
0.6614	Remote Similarity	NPD8328	Phase 3
0.6612	Remote Similarity	NPD8297	Approved
0.6562	Remote Similarity	NPD7492	Approved
0.6529	Remote Similarity	NPD6649	Approved
0.6529	Remote Similarity	NPD6650	Approved
0.6512	Remote Similarity	NPD6616	Approved
0.6508	Remote Similarity	NPD6054	Approved
0.65	Remote Similarity	NPD6373	Approved
0.65	Remote Similarity	NPD6372	Approved
0.6489	Remote Similarity	NPD7319	Approved
0.6462	Remote Similarity	NPD7078	Approved
0.6457	Remote Similarity	NPD8513	Phase 3
0.6457	Remote Similarity	NPD8515	Approved
0.6457	Remote Similarity	NPD8516	Approved
0.6457	Remote Similarity	NPD8517	Approved
0.6455	Remote Similarity	NPD1695	Approved
0.6435	Remote Similarity	NPD4225	Approved
0.6417	Remote Similarity	NPD6899	Approved
0.6417	Remote Similarity	NPD6881	Approved
0.6412	Remote Similarity	NPD7736	Approved
0.6406	Remote Similarity	NPD6370	Approved
0.6389	Remote Similarity	NPD1694	Approved
0.6387	Remote Similarity	NPD6402	Approved
0.6387	Remote Similarity	NPD5739	Approved
0.6387	Remote Similarity	NPD6675	Approved
0.6387	Remote Similarity	NPD7128	Approved
0.6378	Remote Similarity	NPD6059	Approved
0.6357	Remote Similarity	NPD7604	Phase 2
0.6357	Remote Similarity	NPD7642	Approved
0.6341	Remote Similarity	NPD6882	Approved
0.6336	Remote Similarity	NPD8293	Discontinued
0.6333	Remote Similarity	NPD5697	Approved
0.6328	Remote Similarity	NPD6016	Approved
0.6328	Remote Similarity	NPD6015	Approved
0.6325	Remote Similarity	NPD1700	Approved
0.6316	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7102	Approved
0.6311	Remote Similarity	NPD7290	Approved
0.6311	Remote Similarity	NPD6883	Approved
0.6293	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4632	Approved
0.6283	Remote Similarity	NPD5778	Approved
0.6283	Remote Similarity	NPD5779	Approved
0.6281	Remote Similarity	NPD7320	Approved
0.6281	Remote Similarity	NPD6686	Approved
0.6279	Remote Similarity	NPD5988	Approved
0.627	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6009	Approved
0.626	Remote Similarity	NPD8130	Phase 1
0.626	Remote Similarity	NPD7507	Approved
0.626	Remote Similarity	NPD6617	Approved
0.626	Remote Similarity	NPD6847	Approved
0.626	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD3168	Discontinued
0.623	Remote Similarity	NPD6012	Approved
0.623	Remote Similarity	NPD6013	Approved
0.623	Remote Similarity	NPD6014	Approved
0.6228	Remote Similarity	NPD5282	Discontinued
0.6212	Remote Similarity	NPD8074	Phase 3
0.6202	Remote Similarity	NPD5983	Phase 2
0.6198	Remote Similarity	NPD5701	Approved
0.6159	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7638	Approved
0.6148	Remote Similarity	NPD7260	Phase 2
0.6148	Remote Similarity	NPD6011	Approved
0.6136	Remote Similarity	NPD6336	Discontinued
0.6107	Remote Similarity	NPD7830	Approved
0.6107	Remote Similarity	NPD7829	Approved
0.6102	Remote Similarity	NPD7639	Approved
0.6102	Remote Similarity	NPD7640	Approved
0.6087	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7900	Approved
0.608	Remote Similarity	NPD6053	Discontinued
0.6048	Remote Similarity	NPD4634	Approved
0.6047	Remote Similarity	NPD7516	Approved
0.6014	Remote Similarity	NPD8415	Approved
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD8338	Approved
0.5983	Remote Similarity	NPD7839	Suspended
0.5982	Remote Similarity	NPD3573	Approved
0.5969	Remote Similarity	NPD7328	Approved
0.5969	Remote Similarity	NPD7327	Approved
0.5965	Remote Similarity	NPD5785	Approved
0.5963	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6274	Approved
0.5932	Remote Similarity	NPD7902	Approved
0.5929	Remote Similarity	NPD5737	Approved
0.5929	Remote Similarity	NPD6672	Approved
0.5926	Remote Similarity	NPD6033	Approved
0.5923	Remote Similarity	NPD7101	Approved
0.5923	Remote Similarity	NPD7100	Approved
0.5913	Remote Similarity	NPD5693	Phase 1
0.5909	Remote Similarity	NPD6110	Phase 1
0.5877	Remote Similarity	NPD6101	Approved
0.5877	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6845	Suspended
0.5868	Remote Similarity	NPD5211	Phase 2
0.5846	Remote Similarity	NPD6335	Approved
0.584	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5285	Approved
0.5833	Remote Similarity	NPD5286	Approved
0.5833	Remote Similarity	NPD4696	Approved
0.5818	Remote Similarity	NPD5209	Approved
0.5812	Remote Similarity	NPD7748	Approved
0.5804	Remote Similarity	NPD5363	Approved
0.58	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD6084	Phase 2
0.5798	Remote Similarity	NPD6083	Phase 2
0.5798	Remote Similarity	NPD4755	Approved
0.5789	Remote Similarity	NPD8080	Discontinued
0.5781	Remote Similarity	NPD8133	Approved
0.5778	Remote Similarity	NPD8273	Phase 1
0.5778	Remote Similarity	NPD8451	Approved
0.5776	Remote Similarity	NPD6411	Approved
0.5772	Remote Similarity	NPD5141	Approved
0.5769	Remote Similarity	NPD6317	Approved
0.5763	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD5695	Phase 3
0.5752	Remote Similarity	NPD5786	Approved
0.575	Remote Similarity	NPD5696	Approved
0.5739	Remote Similarity	NPD6904	Approved
0.5739	Remote Similarity	NPD6080	Approved
0.5739	Remote Similarity	NPD6673	Approved
0.5738	Remote Similarity	NPD5226	Approved
0.5738	Remote Similarity	NPD5225	Approved
0.5738	Remote Similarity	NPD5224	Approved
0.5738	Remote Similarity	NPD4633	Approved
0.5735	Remote Similarity	NPD8448	Approved
0.5726	Remote Similarity	NPD6399	Phase 3
0.5726	Remote Similarity	NPD5357	Phase 1
0.5725	Remote Similarity	NPD7641	Discontinued
0.5725	Remote Similarity	NPD6313	Approved
0.5725	Remote Similarity	NPD6314	Approved
0.5714	Remote Similarity	NPD8444	Approved
0.5714	Remote Similarity	NPD6908	Approved
0.5714	Remote Similarity	NPD6909	Approved
0.5714	Remote Similarity	NPD8378	Approved
0.5714	Remote Similarity	NPD8380	Approved
0.5714	Remote Similarity	NPD8296	Approved
0.5714	Remote Similarity	NPD8379	Approved
0.5714	Remote Similarity	NPD8033	Approved
0.5714	Remote Similarity	NPD8335	Approved
0.5702	Remote Similarity	NPD4700	Approved
0.5697	Remote Similarity	NPD8368	Discontinued
0.5692	Remote Similarity	NPD6868	Approved
0.5691	Remote Similarity	NPD5174	Approved
0.5691	Remote Similarity	NPD5175	Approved
0.5669	Remote Similarity	NPD2067	Discontinued
0.5656	Remote Similarity	NPD5223	Approved
0.5649	Remote Similarity	NPD7500	Approved
0.5641	Remote Similarity	NPD6050	Approved
0.5641	Remote Similarity	NPD7515	Phase 2
0.5639	Remote Similarity	NPD8377	Approved
0.5639	Remote Similarity	NPD8294	Approved
0.5638	Remote Similarity	NPD6190	Approved
0.5635	Remote Similarity	NPD4729	Approved
0.5635	Remote Similarity	NPD4730	Approved
0.5614	Remote Similarity	NPD5330	Approved
0.5614	Remote Similarity	NPD7521	Approved
0.5614	Remote Similarity	NPD7334	Approved
0.5614	Remote Similarity	NPD7146	Approved
0.5614	Remote Similarity	NPD6684	Approved
0.5614	Remote Similarity	NPD6409	Approved
0.5612	Remote Similarity	NPD8391	Approved
0.5612	Remote Similarity	NPD8390	Approved
0.5612	Remote Similarity	NPD8392	Approved
0.561	Remote Similarity	NPD8300	Approved
0.561	Remote Similarity	NPD7632	Discontinued
0.561	Remote Similarity	NPD8301	Approved
0.56	Remote Similarity	NPD4768	Approved
0.56	Remote Similarity	NPD4767	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