NPASS Compound

Structure

CID179659 OpenBabel06191715552D 27 27 0 0 1 0 0 0 0 0999 V2000 6.6876 2.4719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2662 3.0138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6901 0.9079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2419 1.2133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3984 2.2010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3084 0.8549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6212 2.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1762 1.6678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3990 2.2971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5976 1.1259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8869 1.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7112 4.1764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5312 1.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1098 2.0262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7777 3.8180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8205 1.7552 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4655 1.9387 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8677 5.1641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0005 4.4473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9769 2.7429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3117 2.5681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.5878 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 15 1 0 0 0 0 2 16 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 15 2 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 16 2 0 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 17 23 2 0 0 0 0 18 24 1 1 0 0 0 19 21 1 0 0 0 0 19 25 1 6 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 21 3 1 1 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.24
Volume:	405.411
LogP:	1.591
LogD:	1.689
LogS:	-3.702
# Rotatable Bonds:	12
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	4.403
Fsp3:	0.714
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:	-4.782
MDCK Permeability:	4.714422902907245e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.946
20% Bioavailability (F20%):	0.057
30% Bioavailability (F30%):	0.909

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.742
Plasma Protein Binding (PPB):	69.91483306884766%
Volume Distribution (VD):	0.413
Pgp-substrate:	33.087303161621094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.118
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	6.732
Half-life (T1/2):	0.94

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.643
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.901
Carcinogencity:	0.075
Eye Corrosion:	0.004
Eye Irritation:	0.046
Respiratory Toxicity:	0.32

Download Data

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

Natural Product: NPC179659

Natural Product ID:	NPC179659
*Common Name:**	Ircinolin A
IUPAC Name:	(5S)-5-methyl-5-[(1R,4E,6S,8E)-1,6,14-trihydroxy-4,8-dimethyl-13-oxotetradeca-4,8-dienyl]oxolan-2-one
Synonyms:	Ircinolin A
Standard InCHIKey:	YKUZFPGHZVFVLY-DZMSUEBXSA-N
Standard InCHI:	InChI=1S/C21H34O6/c1-15(6-4-5-7-17(23)14-22)12-18(24)13-16(2)8-9-19(25)21(3)11-10-20(26)27-21/h6,13,18-19,22,24-25H,4-5,7-12,14H2,1-3H3/b15-6+,16-13+/t18-,19+,21-/m0/s1
SMILES:	OCC(=O)CCC/C=C(/C[C@@H](/C=C(/CC[C@H]([C@]1(C)CCC(=O)O1)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823119
PubChem CID:	54672087
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO30704	Ircinia	Genus	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21902186]

☑ 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	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
NPT111	Cell Line	K562	Homo sapiens	IC50	>	20000.0	nM	PMID[528412]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	>	20000.0	nM	PMID[528412]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20000.0	nM	PMID[528412]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[528412]

☑ 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 NPC179659 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	181
0.1-0.2	1140
0.2-0.3	4863
0.3-0.4	10469
0.4-0.5	13633
0.5-0.6	7465
0.6-0.7	3882
0.7-0.8	992
0.8-0.85	60
0.85-0.9	11
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC474761
0.875	High Similarity	NPC476004
0.8652	High Similarity	NPC30515
0.8605	High Similarity	NPC21469
0.8571	High Similarity	NPC36954
0.8556	High Similarity	NPC475912
0.8539	High Similarity	NPC51004
0.8495	Intermediate Similarity	NPC300584
0.8462	Intermediate Similarity	NPC81386
0.8462	Intermediate Similarity	NPC474035
0.8444	Intermediate Similarity	NPC184463
0.8427	Intermediate Similarity	NPC474032
0.8427	Intermediate Similarity	NPC307411
0.8391	Intermediate Similarity	NPC475206
0.8387	Intermediate Similarity	NPC20066
0.837	Intermediate Similarity	NPC270013
0.837	Intermediate Similarity	NPC14961
0.8352	Intermediate Similarity	NPC162205
0.8352	Intermediate Similarity	NPC288240
0.8352	Intermediate Similarity	NPC295204
0.8352	Intermediate Similarity	NPC273579
0.8352	Intermediate Similarity	NPC179746
0.8352	Intermediate Similarity	NPC81419
0.8352	Intermediate Similarity	NPC476300
0.8333	Intermediate Similarity	NPC472755
0.8333	Intermediate Similarity	NPC166554
0.8316	Intermediate Similarity	NPC472753
0.8315	Intermediate Similarity	NPC202672
0.828	Intermediate Similarity	NPC476315
0.8242	Intermediate Similarity	NPC12172
0.8242	Intermediate Similarity	NPC208886
0.8229	Intermediate Similarity	NPC472754
0.8202	Intermediate Similarity	NPC471738
0.8182	Intermediate Similarity	NPC137033
0.8163	Intermediate Similarity	NPC472751
0.8163	Intermediate Similarity	NPC472749
0.8152	Intermediate Similarity	NPC469692
0.8152	Intermediate Similarity	NPC212486
0.8152	Intermediate Similarity	NPC469645
0.8144	Intermediate Similarity	NPC472750
0.8144	Intermediate Similarity	NPC475945
0.8144	Intermediate Similarity	NPC475871
0.8144	Intermediate Similarity	NPC472747
0.8132	Intermediate Similarity	NPC265856
0.8132	Intermediate Similarity	NPC316228
0.8132	Intermediate Similarity	NPC313670
0.8125	Intermediate Similarity	NPC128733
0.8125	Intermediate Similarity	NPC474742
0.8125	Intermediate Similarity	NPC185141
0.8125	Intermediate Similarity	NPC476270
0.8125	Intermediate Similarity	NPC110443
0.8125	Intermediate Similarity	NPC133907
0.8125	Intermediate Similarity	NPC46998
0.8111	Intermediate Similarity	NPC227379
0.8111	Intermediate Similarity	NPC472008
0.8111	Intermediate Similarity	NPC153805
0.8111	Intermediate Similarity	NPC474471
0.809	Intermediate Similarity	NPC112685
0.8068	Intermediate Similarity	NPC475963
0.8068	Intermediate Similarity	NPC243618
0.8068	Intermediate Similarity	NPC474780
0.8068	Intermediate Similarity	NPC70424
0.8068	Intermediate Similarity	NPC474776
0.8068	Intermediate Similarity	NPC3464
0.8068	Intermediate Similarity	NPC151176
0.8065	Intermediate Similarity	NPC57405
0.8065	Intermediate Similarity	NPC303942
0.8065	Intermediate Similarity	NPC121825
0.8061	Intermediate Similarity	NPC472748
0.8061	Intermediate Similarity	NPC472756
0.8043	Intermediate Similarity	NPC146852
0.8043	Intermediate Similarity	NPC473321
0.8041	Intermediate Similarity	NPC474747
0.8041	Intermediate Similarity	NPC324017
0.8041	Intermediate Similarity	NPC320019
0.8041	Intermediate Similarity	NPC149371
0.8023	Intermediate Similarity	NPC470947
0.8023	Intermediate Similarity	NPC103634
0.8023	Intermediate Similarity	NPC470945
0.8023	Intermediate Similarity	NPC472948
0.8023	Intermediate Similarity	NPC200446
0.8023	Intermediate Similarity	NPC470946
0.8022	Intermediate Similarity	NPC474951
0.8022	Intermediate Similarity	NPC295312
0.8022	Intermediate Similarity	NPC173926
0.8	Intermediate Similarity	NPC248602
0.8	Intermediate Similarity	NPC472007
0.7979	Intermediate Similarity	NPC472469
0.7979	Intermediate Similarity	NPC107476
0.7957	Intermediate Similarity	NPC11456
0.7957	Intermediate Similarity	NPC61275
0.7955	Intermediate Similarity	NPC11620
0.7938	Intermediate Similarity	NPC15993
0.7938	Intermediate Similarity	NPC47880
0.7935	Intermediate Similarity	NPC473619
0.7917	Intermediate Similarity	NPC471144
0.7912	Intermediate Similarity	NPC473715
0.7912	Intermediate Similarity	NPC58219
0.7912	Intermediate Similarity	NPC177629
0.7907	Intermediate Similarity	NPC209995
0.7895	Intermediate Similarity	NPC39859
0.7895	Intermediate Similarity	NPC76862
0.7895	Intermediate Similarity	NPC470883
0.7895	Intermediate Similarity	NPC158416
0.7895	Intermediate Similarity	NPC473859
0.7889	Intermediate Similarity	NPC210218
0.7889	Intermediate Similarity	NPC134807
0.7889	Intermediate Similarity	NPC219498
0.7889	Intermediate Similarity	NPC473687
0.7889	Intermediate Similarity	NPC472009
0.7889	Intermediate Similarity	NPC308412
0.7889	Intermediate Similarity	NPC204686
0.7889	Intermediate Similarity	NPC164393
0.7889	Intermediate Similarity	NPC477010
0.7889	Intermediate Similarity	NPC134885
0.7879	Intermediate Similarity	NPC475676
0.7879	Intermediate Similarity	NPC258532
0.7879	Intermediate Similarity	NPC100487
0.7879	Intermediate Similarity	NPC474741
0.7879	Intermediate Similarity	NPC220964
0.7872	Intermediate Similarity	NPC190294
0.7865	Intermediate Similarity	NPC9868
0.7865	Intermediate Similarity	NPC472957
0.7865	Intermediate Similarity	NPC472958
0.7849	Intermediate Similarity	NPC476705
0.7849	Intermediate Similarity	NPC208839
0.7841	Intermediate Similarity	NPC474252
0.7835	Intermediate Similarity	NPC475949
0.7835	Intermediate Similarity	NPC288876
0.7826	Intermediate Similarity	NPC477011
0.7826	Intermediate Similarity	NPC280612
0.7826	Intermediate Similarity	NPC92974
0.7826	Intermediate Similarity	NPC473564
0.7812	Intermediate Similarity	NPC17326
0.7812	Intermediate Similarity	NPC323421
0.7812	Intermediate Similarity	NPC328562
0.7812	Intermediate Similarity	NPC134454
0.7802	Intermediate Similarity	NPC186148
0.7802	Intermediate Similarity	NPC474765
0.7802	Intermediate Similarity	NPC477959
0.7802	Intermediate Similarity	NPC86005
0.7802	Intermediate Similarity	NPC231889
0.7791	Intermediate Similarity	NPC469495
0.7791	Intermediate Similarity	NPC11796
0.7791	Intermediate Similarity	NPC218817
0.7789	Intermediate Similarity	NPC475900
0.7789	Intermediate Similarity	NPC475659
0.7778	Intermediate Similarity	NPC231009
0.7778	Intermediate Similarity	NPC1083
0.7778	Intermediate Similarity	NPC66346
0.7778	Intermediate Similarity	NPC283085
0.7778	Intermediate Similarity	NPC100921
0.7778	Intermediate Similarity	NPC107986
0.7778	Intermediate Similarity	NPC329749
0.7778	Intermediate Similarity	NPC475873
0.7778	Intermediate Similarity	NPC4620
0.7778	Intermediate Similarity	NPC103284
0.7778	Intermediate Similarity	NPC473651
0.7778	Intermediate Similarity	NPC132496
0.7778	Intermediate Similarity	NPC223871
0.7778	Intermediate Similarity	NPC110710
0.7778	Intermediate Similarity	NPC286338
0.7778	Intermediate Similarity	NPC477018
0.7778	Intermediate Similarity	NPC82795
0.7778	Intermediate Similarity	NPC473669
0.7778	Intermediate Similarity	NPC473478
0.7755	Intermediate Similarity	NPC474339
0.7755	Intermediate Similarity	NPC201718
0.7755	Intermediate Similarity	NPC164598
0.7753	Intermediate Similarity	NPC144415
0.7753	Intermediate Similarity	NPC250315
0.7745	Intermediate Similarity	NPC141350
0.7745	Intermediate Similarity	NPC38154
0.7742	Intermediate Similarity	NPC158388
0.7742	Intermediate Similarity	NPC71533
0.7742	Intermediate Similarity	NPC475748
0.7742	Intermediate Similarity	NPC478004
0.7742	Intermediate Similarity	NPC478003
0.7742	Intermediate Similarity	NPC473448
0.7742	Intermediate Similarity	NPC106510
0.7742	Intermediate Similarity	NPC65359
0.7742	Intermediate Similarity	NPC471399
0.7732	Intermediate Similarity	NPC187268
0.7732	Intermediate Similarity	NPC473326
0.7732	Intermediate Similarity	NPC474213
0.7727	Intermediate Similarity	NPC470241
0.7723	Intermediate Similarity	NPC477513
0.7717	Intermediate Similarity	NPC476708
0.7717	Intermediate Similarity	NPC281516
0.7708	Intermediate Similarity	NPC93271
0.7708	Intermediate Similarity	NPC21302
0.7708	Intermediate Similarity	NPC11396
0.7708	Intermediate Similarity	NPC477921
0.7708	Intermediate Similarity	NPC135576
0.7708	Intermediate Similarity	NPC476009
0.7708	Intermediate Similarity	NPC31645
0.7708	Intermediate Similarity	NPC279621
0.7692	Intermediate Similarity	NPC474949
0.7692	Intermediate Similarity	NPC309211
0.7692	Intermediate Similarity	NPC231096

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 NPC179659 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1743
0.2-0.3	3786
0.3-0.4	2281
0.4-0.5	696
0.5-0.6	359
0.6-0.7	90
0.7-0.8	20
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
0.8043	Intermediate Similarity	NPD7983	Approved
0.7692	Intermediate Similarity	NPD5786	Approved
0.7556	Intermediate Similarity	NPD7154	Phase 3
0.7553	Intermediate Similarity	NPD6698	Approved
0.7553	Intermediate Similarity	NPD46	Approved
0.7444	Intermediate Similarity	NPD4269	Approved
0.7444	Intermediate Similarity	NPD4270	Approved
0.7429	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5779	Approved
0.7396	Intermediate Similarity	NPD5778	Approved
0.7391	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5362	Discontinued
0.7333	Intermediate Similarity	NPD5369	Approved
0.7253	Intermediate Similarity	NPD6435	Approved
0.7222	Intermediate Similarity	NPD4252	Approved
0.7204	Intermediate Similarity	NPD5363	Approved
0.7191	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6110	Phase 1
0.7172	Intermediate Similarity	NPD7839	Suspended
0.717	Intermediate Similarity	NPD6371	Approved
0.7073	Intermediate Similarity	NPD3197	Phase 1
0.7053	Intermediate Similarity	NPD4251	Approved
0.7053	Intermediate Similarity	NPD4250	Approved
0.7033	Intermediate Similarity	NPD4820	Approved
0.7033	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4819	Approved
0.7033	Intermediate Similarity	NPD5368	Approved
0.7033	Intermediate Similarity	NPD4821	Approved
0.7033	Intermediate Similarity	NPD4822	Approved
0.7024	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5785	Approved
0.6947	Remote Similarity	NPD4249	Approved
0.69	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8515	Approved
0.6842	Remote Similarity	NPD8517	Approved
0.6842	Remote Similarity	NPD8516	Approved
0.6842	Remote Similarity	NPD8513	Phase 3
0.6837	Remote Similarity	NPD7838	Discovery
0.6813	Remote Similarity	NPD4268	Approved
0.6813	Remote Similarity	NPD4271	Approved
0.6809	Remote Similarity	NPD5331	Approved
0.6809	Remote Similarity	NPD5332	Approved
0.68	Remote Similarity	NPD5282	Discontinued
0.6774	Remote Similarity	NPD4790	Discontinued
0.6735	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5370	Suspended
0.6735	Remote Similarity	NPD6101	Approved
0.6706	Remote Similarity	NPD7331	Phase 2
0.6703	Remote Similarity	NPD4756	Discovery
0.6702	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6411	Approved
0.66	Remote Similarity	NPD7637	Suspended
0.66	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD8074	Phase 3
0.6535	Remote Similarity	NPD6399	Phase 3
0.6518	Remote Similarity	NPD4632	Approved
0.6514	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6686	Approved
0.6491	Remote Similarity	NPD7115	Discovery
0.6481	Remote Similarity	NPD6402	Approved
0.6481	Remote Similarity	NPD5739	Approved
0.6481	Remote Similarity	NPD7128	Approved
0.6481	Remote Similarity	NPD6675	Approved
0.6455	Remote Similarity	NPD6372	Approved
0.6455	Remote Similarity	NPD6373	Approved
0.6442	Remote Similarity	NPD6084	Phase 2
0.6442	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD8297	Approved
0.6429	Remote Similarity	NPD6422	Discontinued
0.6415	Remote Similarity	NPD5344	Discontinued
0.64	Remote Similarity	NPD1695	Approved
0.6364	Remote Similarity	NPD6881	Approved
0.6364	Remote Similarity	NPD7320	Approved
0.6364	Remote Similarity	NPD6899	Approved
0.6364	Remote Similarity	NPD7524	Approved
0.6346	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6650	Approved
0.6339	Remote Similarity	NPD6649	Approved
0.6325	Remote Similarity	NPD6319	Approved
0.6321	Remote Similarity	NPD7640	Approved
0.6321	Remote Similarity	NPD7639	Approved
0.631	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8039	Approved
0.6293	Remote Similarity	NPD7641	Discontinued
0.6273	Remote Similarity	NPD5701	Approved
0.6273	Remote Similarity	NPD5697	Approved
0.6265	Remote Similarity	NPD6109	Phase 1
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD8299	Approved
0.625	Remote Similarity	NPD7492	Approved
0.625	Remote Similarity	NPD8342	Approved
0.625	Remote Similarity	NPD8341	Approved
0.625	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD8340	Approved
0.6226	Remote Similarity	NPD7638	Approved
0.6226	Remote Similarity	NPD5696	Approved
0.6224	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6011	Approved
0.6207	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7341	Phase 2
0.6207	Remote Similarity	NPD6009	Approved
0.6198	Remote Similarity	NPD6616	Approved
0.6195	Remote Similarity	NPD6847	Approved
0.6195	Remote Similarity	NPD6869	Approved
0.6195	Remote Similarity	NPD8130	Phase 1
0.6195	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6617	Approved
0.6186	Remote Similarity	NPD6059	Approved
0.6186	Remote Similarity	NPD6054	Approved
0.6182	Remote Similarity	NPD6008	Approved
0.6167	Remote Similarity	NPD7604	Phase 2
0.6167	Remote Similarity	NPD7642	Approved
0.6167	Remote Similarity	NPD8328	Phase 3
0.6162	Remote Similarity	NPD1696	Phase 3
0.6162	Remote Similarity	NPD1694	Approved
0.6161	Remote Similarity	NPD6014	Approved
0.6161	Remote Similarity	NPD6012	Approved
0.6161	Remote Similarity	NPD6013	Approved
0.6148	Remote Similarity	NPD7078	Approved
0.6148	Remote Similarity	NPD8293	Discontinued
0.6146	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6882	Approved
0.6139	Remote Similarity	NPD5737	Approved
0.6139	Remote Similarity	NPD6672	Approved
0.6136	Remote Similarity	NPD3704	Approved
0.6134	Remote Similarity	NPD5983	Phase 2
0.6134	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8444	Approved
0.6126	Remote Similarity	NPD6412	Phase 2
0.6122	Remote Similarity	NPD6695	Phase 3
0.6106	Remote Similarity	NPD6421	Discontinued
0.6098	Remote Similarity	NPD7736	Approved
0.6094	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7909	Approved
0.6083	Remote Similarity	NPD8080	Discontinued
0.6083	Remote Similarity	NPD6370	Approved
0.608	Remote Similarity	NPD7260	Phase 2
0.6068	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD8451	Approved
0.6066	Remote Similarity	NPD6336	Discontinued
0.6066	Remote Similarity	NPD7507	Approved
0.6061	Remote Similarity	NPD4786	Approved
0.6061	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5211	Phase 2
0.6053	Remote Similarity	NPD2204	Approved
0.6038	Remote Similarity	NPD4697	Phase 3
0.602	Remote Similarity	NPD3667	Approved
0.602	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6648	Approved
0.6018	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD6016	Approved
0.5983	Remote Similarity	NPD2629	Approved
0.5981	Remote Similarity	NPD4755	Approved
0.5981	Remote Similarity	NPD7902	Approved
0.5977	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD3195	Phase 2
0.5976	Remote Similarity	NPD3728	Approved
0.5976	Remote Similarity	NPD4266	Approved
0.5976	Remote Similarity	NPD3730	Approved
0.5976	Remote Similarity	NPD3196	Approved
0.5976	Remote Similarity	NPD3194	Approved
0.5965	Remote Similarity	NPD4634	Approved
0.5962	Remote Similarity	NPD7515	Phase 2
0.595	Remote Similarity	NPD5988	Approved
0.5946	Remote Similarity	NPD5141	Approved
0.5941	Remote Similarity	NPD7334	Approved
0.5941	Remote Similarity	NPD5330	Approved
0.5941	Remote Similarity	NPD7521	Approved
0.5941	Remote Similarity	NPD6098	Approved
0.5941	Remote Similarity	NPD5279	Phase 3
0.5941	Remote Similarity	NPD6684	Approved
0.5941	Remote Similarity	NPD6409	Approved
0.5941	Remote Similarity	NPD7146	Approved
0.5935	Remote Similarity	NPD8273	Phase 1
0.5932	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6904	Approved
0.5922	Remote Similarity	NPD6673	Approved
0.5922	Remote Similarity	NPD4753	Phase 2
0.5922	Remote Similarity	NPD6080	Approved
0.5922	Remote Similarity	NPD5328	Approved
0.592	Remote Similarity	NPD7319	Approved
0.5913	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD6845	Suspended
0.5902	Remote Similarity	NPD7830	Approved
0.5902	Remote Similarity	NPD7829	Approved
0.5893	Remote Similarity	NPD5048	Discontinued
0.5891	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5221	Approved
0.5888	Remote Similarity	NPD5222	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