NPASS Compound

Structure

NPC469551 OpenBabel07101719522D 28 29 0 0 1 0 0 0 0 0999 V2000 6.9282 1.0000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 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 2.5981 -2.5000 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 1.7321 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 1.7321 1.0000 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 6.0622 2.5000 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 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 3 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 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 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 5.1962 1.0000 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 4.3301 2.5000 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 8 1 0 0 0 0 2 12 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 14 2 0 0 0 0 6 15 1 0 0 0 0 8 13 2 0 0 0 0 9 10 1 0 0 0 0 9 12 2 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 14 1 1 0 0 0 16 19 1 0 0 0 0 17 27 1 0 0 0 0 18 22 1 6 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 6 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 25 2 0 0 0 0 21 27 1 0 0 0 0 22 7 1 6 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.2
Volume:	408.878
LogP:	3.077
LogD:	2.279
LogS:	-3.864
# Rotatable Bonds:	9
TPSA:	82.2
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.287
Synthetic Accessibility Score:	4.867
Fsp3:	0.591
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:	-4.58
MDCK Permeability:	3.754697536351159e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.052
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.075
30% Bioavailability (F30%):	0.845

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.875
Plasma Protein Binding (PPB):	73.87303924560547%
Volume Distribution (VD):	2.325
Pgp-substrate:	20.3594913482666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.216
CYP2C19-substrate:	0.69
CYP2C9-inhibitor:	0.117
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.72
CYP3A4-substrate:	0.376

ADMET: Excretion

Clearance (CL):	12.069
Half-life (T1/2):	0.125

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.95
Drug-inuced Liver Injury (DILI):	0.868
AMES Toxicity:	0.226
Rat Oral Acute Toxicity:	0.902
Maximum Recommended Daily Dose:	0.833
Skin Sensitization:	0.402
Carcinogencity:	0.731
Eye Corrosion:	0.923
Eye Irritation:	0.854
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC469551

Natural Product ID:	NPC469551
*Common Name:**	Altaicalarin C
IUPAC Name:	[2-[(1S,3S,4S,6S)-4-acetyloxy-6-methyl-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-6-methylhepta-1,5-dien-3-yl] (Z)-2-methylbut-2-enoate
Synonyms:	altaicalarin C
Standard InCHIKey:	DAQJZMZCFFUHCO-NAFQNHHTSA-N
Standard InCHI:	InChI=1S/C22H30O6/c1-8-13(4)21(25)27-17(10-9-12(2)3)14(5)16-11-18-22(7,28-18)20(24)19(16)26-15(6)23/h8-9,16-19H,5,10-11H2,1-4,6-7H3/b13-8-/t16-,17?,18-,19-,22-/m0/s1
SMILES:	CC=C(C)C(=O)OC(CC=C(C)C)C(=C)C1CC2C(O2)(C(=O)C1OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087039
PubChem CID:	46186620
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
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	7.7	ug.mL-1	PMID[453231]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	10.4	ug.mL-1	PMID[453231]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	11.4	ug.mL-1	PMID[453231]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	7.6	ug.mL-1	PMID[453231]

☑ 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 NPC469551 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	257
0.1-0.2	1625
0.2-0.3	4946
0.3-0.4	8396
0.4-0.5	14647
0.5-0.6	8353
0.6-0.7	3737
0.7-0.8	692
0.8-0.85	37
0.85-0.9	1
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC474716
0.9	High Similarity	NPC469558
0.8673	High Similarity	NPC264378
0.8632	High Similarity	NPC20713
0.8511	High Similarity	NPC475902
0.8286	Intermediate Similarity	NPC471934
0.8283	Intermediate Similarity	NPC476275
0.8224	Intermediate Similarity	NPC471933
0.8211	Intermediate Similarity	NPC475087
0.819	Intermediate Similarity	NPC322903
0.8173	Intermediate Similarity	NPC103088
0.8173	Intermediate Similarity	NPC470979
0.8173	Intermediate Similarity	NPC470975
0.8165	Intermediate Similarity	NPC477509
0.8148	Intermediate Similarity	NPC159333
0.8144	Intermediate Similarity	NPC469718
0.8144	Intermediate Similarity	NPC329857
0.8137	Intermediate Similarity	NPC477511
0.8137	Intermediate Similarity	NPC264477
0.81	Intermediate Similarity	NPC17585
0.8081	Intermediate Similarity	NPC140543
0.8058	Intermediate Similarity	NPC39996
0.8041	Intermediate Similarity	NPC166919
0.8037	Intermediate Similarity	NPC253906
0.8	Intermediate Similarity	NPC474947
0.8	Intermediate Similarity	NPC270478
0.8	Intermediate Similarity	NPC474547
0.7982	Intermediate Similarity	NPC473802
0.7982	Intermediate Similarity	NPC33360
0.7963	Intermediate Similarity	NPC317107
0.7961	Intermediate Similarity	NPC474339
0.7961	Intermediate Similarity	NPC476478
0.7961	Intermediate Similarity	NPC201718
0.7961	Intermediate Similarity	NPC164598
0.7938	Intermediate Similarity	NPC471047
0.7938	Intermediate Similarity	NPC469628
0.7938	Intermediate Similarity	NPC475906
0.7938	Intermediate Similarity	NPC469653
0.7938	Intermediate Similarity	NPC469631
0.7925	Intermediate Similarity	NPC475510
0.7925	Intermediate Similarity	NPC475587
0.7925	Intermediate Similarity	NPC266514
0.7913	Intermediate Similarity	NPC473709
0.7913	Intermediate Similarity	NPC473919
0.7905	Intermediate Similarity	NPC474741
0.7905	Intermediate Similarity	NPC471143
0.7905	Intermediate Similarity	NPC477127
0.7905	Intermediate Similarity	NPC477510
0.79	Intermediate Similarity	NPC476267
0.789	Intermediate Similarity	NPC317687
0.7879	Intermediate Similarity	NPC473944
0.787	Intermediate Similarity	NPC473594
0.787	Intermediate Similarity	NPC474586
0.787	Intermediate Similarity	NPC473975
0.787	Intermediate Similarity	NPC473843
0.7864	Intermediate Similarity	NPC477512
0.7857	Intermediate Similarity	NPC475971
0.785	Intermediate Similarity	NPC473939
0.785	Intermediate Similarity	NPC473595
0.7845	Intermediate Similarity	NPC471939
0.7843	Intermediate Similarity	NPC474921
0.7843	Intermediate Similarity	NPC471140
0.7835	Intermediate Similarity	NPC231889
0.7835	Intermediate Similarity	NPC471739
0.7835	Intermediate Similarity	NPC475703
0.7826	Intermediate Similarity	NPC472399
0.7822	Intermediate Similarity	NPC470978
0.7822	Intermediate Similarity	NPC470974
0.7798	Intermediate Similarity	NPC96739
0.7798	Intermediate Similarity	NPC174471
0.7798	Intermediate Similarity	NPC194619
0.7798	Intermediate Similarity	NPC260786
0.7798	Intermediate Similarity	NPC474871
0.7789	Intermediate Similarity	NPC170377
0.7789	Intermediate Similarity	NPC272814
0.7788	Intermediate Similarity	NPC207885
0.7788	Intermediate Similarity	NPC476270
0.7788	Intermediate Similarity	NPC112613
0.7778	Intermediate Similarity	NPC469370
0.7778	Intermediate Similarity	NPC475748
0.7778	Intermediate Similarity	NPC62815
0.7778	Intermediate Similarity	NPC471940
0.7767	Intermediate Similarity	NPC471932
0.7766	Intermediate Similarity	NPC286229
0.7757	Intermediate Similarity	NPC180744
0.7757	Intermediate Similarity	NPC477513
0.7745	Intermediate Similarity	NPC118159
0.7745	Intermediate Similarity	NPC94337
0.7742	Intermediate Similarity	NPC471740
0.7732	Intermediate Similarity	NPC50637
0.7727	Intermediate Similarity	NPC215643
0.7727	Intermediate Similarity	NPC101825
0.7727	Intermediate Similarity	NPC265499
0.7727	Intermediate Similarity	NPC89227
0.7727	Intermediate Similarity	NPC170212
0.7727	Intermediate Similarity	NPC151216
0.7727	Intermediate Similarity	NPC17138
0.7727	Intermediate Similarity	NPC221511
0.7727	Intermediate Similarity	NPC475391
0.7723	Intermediate Similarity	NPC471147
0.7723	Intermediate Similarity	NPC470697
0.7723	Intermediate Similarity	NPC473316
0.7723	Intermediate Similarity	NPC473330
0.7714	Intermediate Similarity	NPC149371
0.7714	Intermediate Similarity	NPC162973
0.7706	Intermediate Similarity	NPC89408
0.7706	Intermediate Similarity	NPC281624
0.7699	Intermediate Similarity	NPC470420
0.7699	Intermediate Similarity	NPC240509
0.7692	Intermediate Similarity	NPC288876
0.7692	Intermediate Similarity	NPC474718
0.7685	Intermediate Similarity	NPC476479
0.7679	Intermediate Similarity	NPC476710
0.7679	Intermediate Similarity	NPC476711
0.7677	Intermediate Similarity	NPC151770
0.7664	Intermediate Similarity	NPC1679
0.766	Intermediate Similarity	NPC474510
0.7658	Intermediate Similarity	NPC474937
0.7658	Intermediate Similarity	NPC470120
0.7658	Intermediate Similarity	NPC71889
0.7658	Intermediate Similarity	NPC477126
0.7653	Intermediate Similarity	NPC471738
0.7652	Intermediate Similarity	NPC472401
0.7647	Intermediate Similarity	NPC475659
0.7647	Intermediate Similarity	NPC469583
0.7647	Intermediate Similarity	NPC56369
0.7642	Intermediate Similarity	NPC472755
0.7642	Intermediate Similarity	NPC475945
0.7642	Intermediate Similarity	NPC475871
0.7642	Intermediate Similarity	NPC469980
0.7642	Intermediate Similarity	NPC104161
0.7642	Intermediate Similarity	NPC118902
0.7636	Intermediate Similarity	NPC475495
0.7636	Intermediate Similarity	NPC171888
0.7636	Intermediate Similarity	NPC146945
0.7632	Intermediate Similarity	NPC476107
0.7624	Intermediate Similarity	NPC165383
0.7619	Intermediate Similarity	NPC472753
0.7619	Intermediate Similarity	NPC47880
0.7619	Intermediate Similarity	NPC474742
0.7615	Intermediate Similarity	NPC474242
0.7611	Intermediate Similarity	NPC476713
0.7611	Intermediate Similarity	NPC469684
0.7611	Intermediate Similarity	NPC476712
0.7607	Intermediate Similarity	NPC24651
0.7604	Intermediate Similarity	NPC53867
0.7604	Intermediate Similarity	NPC222358
0.7604	Intermediate Similarity	NPC474703
0.76	Intermediate Similarity	NPC312042
0.7596	Intermediate Similarity	NPC72647
0.7596	Intermediate Similarity	NPC107806
0.7596	Intermediate Similarity	NPC208233
0.7589	Intermediate Similarity	NPC474872
0.7589	Intermediate Similarity	NPC238667
0.7586	Intermediate Similarity	NPC19464
0.7579	Intermediate Similarity	NPC141810
0.7579	Intermediate Similarity	NPC475481
0.7579	Intermediate Similarity	NPC79277
0.7573	Intermediate Similarity	NPC472995
0.7573	Intermediate Similarity	NPC172998
0.7573	Intermediate Similarity	NPC475380
0.7573	Intermediate Similarity	NPC209297
0.7573	Intermediate Similarity	NPC35498
0.7573	Intermediate Similarity	NPC202833
0.7573	Intermediate Similarity	NPC473291
0.7573	Intermediate Similarity	NPC301596
0.7573	Intermediate Similarity	NPC473859
0.7573	Intermediate Similarity	NPC472997
0.7573	Intermediate Similarity	NPC299396
0.7573	Intermediate Similarity	NPC230800
0.7573	Intermediate Similarity	NPC279722
0.7573	Intermediate Similarity	NPC472996
0.757	Intermediate Similarity	NPC470297
0.7568	Intermediate Similarity	NPC277769
0.7568	Intermediate Similarity	NPC473877
0.7568	Intermediate Similarity	NPC4573
0.7568	Intermediate Similarity	NPC477093
0.7568	Intermediate Similarity	NPC473522
0.7568	Intermediate Similarity	NPC475277
0.7565	Intermediate Similarity	NPC471126
0.7565	Intermediate Similarity	NPC157252
0.7565	Intermediate Similarity	NPC471128
0.7565	Intermediate Similarity	NPC145182
0.7563	Intermediate Similarity	NPC236999
0.7563	Intermediate Similarity	NPC476859
0.7553	Intermediate Similarity	NPC276647
0.7553	Intermediate Similarity	NPC622
0.7551	Intermediate Similarity	NPC122502
0.7551	Intermediate Similarity	NPC38576
0.7551	Intermediate Similarity	NPC279859
0.7549	Intermediate Similarity	NPC161998
0.7549	Intermediate Similarity	NPC148463
0.7549	Intermediate Similarity	NPC38830
0.7549	Intermediate Similarity	NPC469632
0.7547	Intermediate Similarity	NPC472754
0.7547	Intermediate Similarity	NPC474747
0.7547	Intermediate Similarity	NPC471148
0.7547	Intermediate Similarity	NPC474709
0.7547	Intermediate Similarity	NPC475750
0.7545	Intermediate Similarity	NPC153036

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 NPC469551 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	2055
0.2-0.3	3691
0.3-0.4	2037
0.4-0.5	800
0.5-0.6	235
0.6-0.7	98
0.7-0.8	3
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
0.7358	Intermediate Similarity	NPD6648	Approved
0.729	Intermediate Similarity	NPD5344	Discontinued
0.7273	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6698	Approved
0.7255	Intermediate Similarity	NPD46	Approved
0.7182	Intermediate Similarity	NPD6008	Approved
0.7117	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.699	Remote Similarity	NPD1695	Approved
0.6975	Remote Similarity	NPD6319	Approved
0.6964	Remote Similarity	NPD5697	Approved
0.6964	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD1694	Approved
0.693	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6881	Approved
0.6903	Remote Similarity	NPD6899	Approved
0.6875	Remote Similarity	NPD7128	Approved
0.6875	Remote Similarity	NPD6402	Approved
0.6875	Remote Similarity	NPD5739	Approved
0.6875	Remote Similarity	NPD6675	Approved
0.6864	Remote Similarity	NPD7115	Discovery
0.6842	Remote Similarity	NPD6014	Approved
0.6842	Remote Similarity	NPD6013	Approved
0.6842	Remote Similarity	NPD6012	Approved
0.6822	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5701	Approved
0.6792	Remote Similarity	NPD5778	Approved
0.6792	Remote Similarity	NPD5779	Approved
0.6783	Remote Similarity	NPD6371	Approved
0.6783	Remote Similarity	NPD7290	Approved
0.6783	Remote Similarity	NPD6883	Approved
0.6783	Remote Similarity	NPD7102	Approved
0.6762	Remote Similarity	NPD7838	Discovery
0.6754	Remote Similarity	NPD7320	Approved
0.6754	Remote Similarity	NPD6011	Approved
0.6748	Remote Similarity	NPD7492	Approved
0.6729	Remote Similarity	NPD5282	Discontinued
0.6724	Remote Similarity	NPD6847	Approved
0.6724	Remote Similarity	NPD6617	Approved
0.6724	Remote Similarity	NPD8130	Phase 1
0.6724	Remote Similarity	NPD6869	Approved
0.6724	Remote Similarity	NPD6649	Approved
0.6724	Remote Similarity	NPD6650	Approved
0.6698	Remote Similarity	NPD7983	Approved
0.6696	Remote Similarity	NPD6372	Approved
0.6696	Remote Similarity	NPD6373	Approved
0.6694	Remote Similarity	NPD6054	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.664	Remote Similarity	NPD7078	Approved
0.6639	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD6016	Approved
0.6636	Remote Similarity	NPD4225	Approved
0.6636	Remote Similarity	NPD7638	Approved
0.6635	Remote Similarity	NPD3573	Approved
0.6634	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4632	Approved
0.6587	Remote Similarity	NPD7736	Approved
0.6585	Remote Similarity	NPD6370	Approved
0.6585	Remote Similarity	NPD5988	Approved
0.6583	Remote Similarity	NPD6009	Approved
0.6577	Remote Similarity	NPD7639	Approved
0.6577	Remote Similarity	NPD7640	Approved
0.6557	Remote Similarity	NPD6059	Approved
0.6542	Remote Similarity	NPD5693	Phase 1
0.6535	Remote Similarity	NPD7319	Approved
0.6532	Remote Similarity	NPD8328	Phase 3
0.6532	Remote Similarity	NPD7604	Phase 2
0.6525	Remote Similarity	NPD6053	Discontinued
0.6522	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD8293	Discontinued
0.6504	Remote Similarity	NPD5983	Phase 2
0.65	Remote Similarity	NPD6274	Approved
0.6496	Remote Similarity	NPD4634	Approved
0.6471	Remote Similarity	NPD5209	Approved
0.646	Remote Similarity	NPD5211	Phase 2
0.6441	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5285	Approved
0.6429	Remote Similarity	NPD5286	Approved
0.6429	Remote Similarity	NPD4696	Approved
0.6422	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7900	Approved
0.6415	Remote Similarity	NPD5737	Approved
0.6415	Remote Similarity	NPD6672	Approved
0.6396	Remote Similarity	NPD4755	Approved
0.6371	Remote Similarity	NPD8513	Phase 3
0.6371	Remote Similarity	NPD6921	Approved
0.6371	Remote Similarity	NPD8517	Approved
0.6371	Remote Similarity	NPD8516	Approved
0.6371	Remote Similarity	NPD8515	Approved
0.6364	Remote Similarity	NPD5695	Phase 3
0.6355	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6101	Approved
0.6348	Remote Similarity	NPD5141	Approved
0.6341	Remote Similarity	NPD7101	Approved
0.6341	Remote Similarity	NPD7100	Approved
0.6325	Remote Similarity	NPD6686	Approved
0.6316	Remote Similarity	NPD5226	Approved
0.6316	Remote Similarity	NPD5225	Approved
0.6316	Remote Similarity	NPD5224	Approved
0.6316	Remote Similarity	NPD4633	Approved
0.6311	Remote Similarity	NPD6317	Approved
0.6306	Remote Similarity	NPD7839	Suspended
0.6299	Remote Similarity	NPD7507	Approved
0.6299	Remote Similarity	NPD6336	Discontinued
0.6296	Remote Similarity	NPD5785	Approved
0.6283	Remote Similarity	NPD4700	Approved
0.6273	Remote Similarity	NPD7748	Approved
0.627	Remote Similarity	NPD7642	Approved
0.6261	Remote Similarity	NPD5175	Approved
0.6261	Remote Similarity	NPD5174	Approved
0.626	Remote Similarity	NPD6335	Approved
0.626	Remote Similarity	NPD6313	Approved
0.626	Remote Similarity	NPD6314	Approved
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD7902	Approved
0.6239	Remote Similarity	NPD6411	Approved
0.6228	Remote Similarity	NPD5223	Approved
0.6204	Remote Similarity	NPD6673	Approved
0.6204	Remote Similarity	NPD6080	Approved
0.6204	Remote Similarity	NPD6904	Approved
0.6195	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5696	Approved
0.6179	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5221	Approved
0.6161	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5222	Approved
0.6147	Remote Similarity	NPD3168	Discontinued
0.6147	Remote Similarity	NPD5692	Phase 3
0.6142	Remote Similarity	NPD7829	Approved
0.6142	Remote Similarity	NPD7830	Approved
0.6139	Remote Similarity	NPD4756	Discovery
0.6132	Remote Similarity	NPD5363	Approved
0.6124	Remote Similarity	NPD8074	Phase 3
0.6111	Remote Similarity	NPD6909	Approved
0.6111	Remote Similarity	NPD6908	Approved
0.6106	Remote Similarity	NPD5173	Approved
0.6098	Remote Similarity	NPD6868	Approved
0.6091	Remote Similarity	NPD6050	Approved
0.6091	Remote Similarity	NPD7515	Phase 2
0.6091	Remote Similarity	NPD5694	Approved
0.6087	Remote Similarity	NPD1700	Approved
0.6077	Remote Similarity	NPD6033	Approved
0.6075	Remote Similarity	NPD6684	Approved
0.6075	Remote Similarity	NPD7521	Approved
0.6075	Remote Similarity	NPD5330	Approved
0.6075	Remote Similarity	NPD6409	Approved
0.6075	Remote Similarity	NPD7146	Approved
0.6075	Remote Similarity	NPD5786	Approved
0.6075	Remote Similarity	NPD7334	Approved
0.6074	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7260	Phase 2
0.605	Remote Similarity	NPD4729	Approved
0.605	Remote Similarity	NPD5128	Approved
0.605	Remote Similarity	NPD4730	Approved
0.6036	Remote Similarity	NPD6399	Phase 3
0.6034	Remote Similarity	NPD7632	Discontinued
0.6018	Remote Similarity	NPD4697	Phase 3
0.6017	Remote Similarity	NPD4767	Approved
0.6017	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD6435	Approved
0.6	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7328	Approved
0.5984	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4754	Approved
0.5963	Remote Similarity	NPD6903	Approved
0.5963	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7516	Approved
0.595	Remote Similarity	NPD5251	Approved
0.595	Remote Similarity	NPD5250	Approved
0.595	Remote Similarity	NPD5247	Approved
0.595	Remote Similarity	NPD5248	Approved
0.595	Remote Similarity	NPD5249	Phase 3
0.5946	Remote Similarity	NPD7637	Suspended
0.5946	Remote Similarity	NPD6079	Approved
0.5943	Remote Similarity	NPD7154	Phase 3
0.5941	Remote Similarity	NPD8039	Approved
0.5926	Remote Similarity	NPD6422	Discontinued
0.5926	Remote Similarity	NPD8415	Approved
0.5926	Remote Similarity	NPD6098	Approved
0.5912	Remote Similarity	NPD6333	Approved
0.5912	Remote Similarity	NPD6334	Approved
0.5909	Remote Similarity	NPD5328	Approved
0.5905	Remote Similarity	NPD5369	Approved
0.5902	Remote Similarity	NPD5215	Approved
0.5902	Remote Similarity	NPD5216	Approved
0.5902	Remote Similarity	NPD5217	Approved
0.5897	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD8338	Approved
0.5849	Remote Similarity	NPD4270	Approved
0.5849	Remote Similarity	NPD4269	Approved
0.5841	Remote Similarity	NPD6001	Approved
0.5833	Remote Similarity	NPD1696	Phase 3
0.5826	Remote Similarity	NPD5959	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