NPASS Compound

Structure

NPC11796 OpenBabel07101718192D 24 24 0 0 1 0 0 0 0 0999 V2000 10.0263 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0263 7.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 7.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 7.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 7.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 7.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 7.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 7.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 7.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 7.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 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 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 18 2 1 6 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 19 17 1 1 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 6 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.28
Volume:	384.313
LogP:	6.304
LogD:	4.255
LogS:	-3.069
# Rotatable Bonds:	14
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.256
Synthetic Accessibility Score:	3.462
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.834
MDCK Permeability:	3.643511081463657e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	98.17526245117188%
Volume Distribution (VD):	1.678
Pgp-substrate:	2.4713613986968994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.385
CYP1A2-substrate:	0.289
CYP2C19-inhibitor:	0.373
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.317
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.2
CYP2D6-substrate:	0.337
CYP3A4-inhibitor:	0.787
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	4.246
Half-life (T1/2):	0.515

ADMET: Toxicity

hERG Blockers:	0.377
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.264
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.951
Carcinogencity:	0.117
Eye Corrosion:	0.494
Eye Irritation:	0.656
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC11796

Natural Product ID:	NPC11796
*Common Name:**	(3S,4S,5S)-3-[(Z)-Hexadec-7-Enyl]-4-Hydroxy-5-Methyloxolan-2-One
IUPAC Name:	(3S,4S,5S)-3-[(Z)-hexadec-7-enyl]-4-hydroxy-5-methyloxolan-2-one
Synonyms:
Standard InCHIKey:	BRHQPRAQLMOAKC-CAYSUEKXSA-N
Standard InCHI:	InChI=1S/C21H38O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-20(22)18(2)24-21(19)23/h10-11,18-20,22H,3-9,12-17H2,1-2H3/b11-10-/t18-,19-,20+/m0/s1
SMILES:	CCCCCCCC/C=CCCCCCC[C@H]1[C@@H]([C@H](C)OC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL381644
PubChem CID:	44404760
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO1241	Laetia procera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16168652]
NPO1241	Laetia procera	Species	Salicaceae	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
Others	6

Activity Type	# Activity
Cell Line	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	65.9	uM	PMID[556051]
NPT83	Cell Line	MCF7	Homo sapiens	Ratio	=	2.1	n.a.	PMID[556051]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	57.6	uM	PMID[556051]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	27.5	uM	PMID[556051]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	=	129.0	uM	PMID[556051]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	=	111.0	uM	PMID[556051]

☑ 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 NPC11796 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	161
0.1-0.2	1104
0.2-0.3	5573
0.3-0.4	15344
0.4-0.5	8694
0.5-0.6	8126
0.6-0.7	3023
0.7-0.8	640
0.8-0.85	21
0.85-0.9	8
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC218817
0.8961	High Similarity	NPC200446
0.8831	High Similarity	NPC209995
0.8701	High Similarity	NPC469495
0.8514	High Similarity	NPC42526
0.8493	Intermediate Similarity	NPC209327
0.8493	Intermediate Similarity	NPC273508
0.8415	Intermediate Similarity	NPC475206
0.8356	Intermediate Similarity	NPC104537
0.8356	Intermediate Similarity	NPC22101
0.8356	Intermediate Similarity	NPC271921
0.8356	Intermediate Similarity	NPC330426
0.8356	Intermediate Similarity	NPC127091
0.8356	Intermediate Similarity	NPC148192
0.8312	Intermediate Similarity	NPC81052
0.825	Intermediate Similarity	NPC469920
0.8243	Intermediate Similarity	NPC473559
0.8243	Intermediate Similarity	NPC324981
0.8243	Intermediate Similarity	NPC48218
0.8243	Intermediate Similarity	NPC141481
0.8182	Intermediate Similarity	NPC472966
0.8108	Intermediate Similarity	NPC475443
0.8108	Intermediate Similarity	NPC473829
0.8095	Intermediate Similarity	NPC469483
0.8095	Intermediate Similarity	NPC477994
0.8095	Intermediate Similarity	NPC477993
0.8077	Intermediate Similarity	NPC217725
0.8026	Intermediate Similarity	NPC476660
0.8025	Intermediate Similarity	NPC103634
0.8025	Intermediate Similarity	NPC472948
0.7975	Intermediate Similarity	NPC469514
0.7975	Intermediate Similarity	NPC470899
0.7955	Intermediate Similarity	NPC469645
0.7955	Intermediate Similarity	NPC469692
0.7952	Intermediate Similarity	NPC475947
0.7931	Intermediate Similarity	NPC478004
0.7931	Intermediate Similarity	NPC158388
0.7931	Intermediate Similarity	NPC313670
0.7931	Intermediate Similarity	NPC478003
0.7927	Intermediate Similarity	NPC47031
0.7907	Intermediate Similarity	NPC476707
0.7907	Intermediate Similarity	NPC476706
0.7907	Intermediate Similarity	NPC476803
0.7895	Intermediate Similarity	NPC473772
0.7895	Intermediate Similarity	NPC199557
0.7882	Intermediate Similarity	NPC469910
0.7875	Intermediate Similarity	NPC281296
0.7867	Intermediate Similarity	NPC469925
0.7865	Intermediate Similarity	NPC121825
0.7841	Intermediate Similarity	NPC184463
0.7831	Intermediate Similarity	NPC7414
0.7831	Intermediate Similarity	NPC474252
0.7821	Intermediate Similarity	NPC167145
0.7791	Intermediate Similarity	NPC179659
0.7778	Intermediate Similarity	NPC121200
0.7765	Intermediate Similarity	NPC125290
0.7753	Intermediate Similarity	NPC478036
0.7753	Intermediate Similarity	NPC478037
0.775	Intermediate Similarity	NPC49392
0.775	Intermediate Similarity	NPC190400
0.775	Intermediate Similarity	NPC279537
0.7727	Intermediate Similarity	NPC15059
0.7727	Intermediate Similarity	NPC474232
0.7722	Intermediate Similarity	NPC330016
0.7722	Intermediate Similarity	NPC474321
0.7711	Intermediate Similarity	NPC470241
0.7701	Intermediate Similarity	NPC201046
0.7701	Intermediate Similarity	NPC476708
0.7692	Intermediate Similarity	NPC474590
0.7692	Intermediate Similarity	NPC477981
0.7692	Intermediate Similarity	NPC477983
0.7683	Intermediate Similarity	NPC19841
0.7683	Intermediate Similarity	NPC89128
0.7683	Intermediate Similarity	NPC470244
0.7683	Intermediate Similarity	NPC469747
0.7683	Intermediate Similarity	NPC263574
0.7683	Intermediate Similarity	NPC201225
0.7683	Intermediate Similarity	NPC470239
0.7674	Intermediate Similarity	NPC475753
0.7671	Intermediate Similarity	NPC174560
0.7671	Intermediate Similarity	NPC125312
0.7671	Intermediate Similarity	NPC201939
0.7662	Intermediate Similarity	NPC144511
0.7662	Intermediate Similarity	NPC296522
0.7654	Intermediate Similarity	NPC474760
0.7654	Intermediate Similarity	NPC7563
0.7654	Intermediate Similarity	NPC116177
0.7654	Intermediate Similarity	NPC320630
0.7647	Intermediate Similarity	NPC9868
0.7647	Intermediate Similarity	NPC158756
0.764	Intermediate Similarity	NPC476705
0.764	Intermediate Similarity	NPC30515
0.7632	Intermediate Similarity	NPC473357
0.7632	Intermediate Similarity	NPC193029
0.7625	Intermediate Similarity	NPC324762
0.7625	Intermediate Similarity	NPC199445
0.7619	Intermediate Similarity	NPC474291
0.7619	Intermediate Similarity	NPC89555
0.7614	Intermediate Similarity	NPC307411
0.7614	Intermediate Similarity	NPC473564
0.7614	Intermediate Similarity	NPC52198
0.7614	Intermediate Similarity	NPC77001
0.7614	Intermediate Similarity	NPC117405
0.7614	Intermediate Similarity	NPC253618
0.7609	Intermediate Similarity	NPC40812
0.76	Intermediate Similarity	NPC476654
0.76	Intermediate Similarity	NPC476655
0.76	Intermediate Similarity	NPC476657
0.759	Intermediate Similarity	NPC233377
0.759	Intermediate Similarity	NPC115418
0.7586	Intermediate Similarity	NPC86005
0.7586	Intermediate Similarity	NPC477959
0.7582	Intermediate Similarity	NPC36954
0.7579	Intermediate Similarity	NPC4620
0.7568	Intermediate Similarity	NPC54925
0.7564	Intermediate Similarity	NPC472955
0.7561	Intermediate Similarity	NPC127526
0.7561	Intermediate Similarity	NPC192006
0.7561	Intermediate Similarity	NPC267231
0.7558	Intermediate Similarity	NPC470755
0.7558	Intermediate Similarity	NPC21469
0.7558	Intermediate Similarity	NPC255307
0.7558	Intermediate Similarity	NPC329738
0.7556	Intermediate Similarity	NPC212486
0.7556	Intermediate Similarity	NPC476300
0.7556	Intermediate Similarity	NPC475912
0.7553	Intermediate Similarity	NPC472753
0.7534	Intermediate Similarity	NPC81896
0.7534	Intermediate Similarity	NPC321919
0.7534	Intermediate Similarity	NPC243532
0.7531	Intermediate Similarity	NPC474447
0.7531	Intermediate Similarity	NPC239127
0.7529	Intermediate Similarity	NPC69469
0.7528	Intermediate Similarity	NPC474761
0.7528	Intermediate Similarity	NPC476004
0.7528	Intermediate Similarity	NPC473448
0.7528	Intermediate Similarity	NPC51004
0.7527	Intermediate Similarity	NPC83895
0.7527	Intermediate Similarity	NPC187761
0.75	Intermediate Similarity	NPC476656
0.75	Intermediate Similarity	NPC202672
0.75	Intermediate Similarity	NPC476805
0.75	Intermediate Similarity	NPC220964
0.75	Intermediate Similarity	NPC473859
0.75	Intermediate Similarity	NPC474551
0.75	Intermediate Similarity	NPC475676
0.75	Intermediate Similarity	NPC52861
0.75	Intermediate Similarity	NPC472756
0.75	Intermediate Similarity	NPC476659
0.75	Intermediate Similarity	NPC88735
0.75	Intermediate Similarity	NPC19136
0.7474	Intermediate Similarity	NPC472754
0.7474	Intermediate Similarity	NPC474747
0.7474	Intermediate Similarity	NPC225353
0.7471	Intermediate Similarity	NPC278283
0.7471	Intermediate Similarity	NPC475461
0.7471	Intermediate Similarity	NPC150755
0.7471	Intermediate Similarity	NPC478112
0.7471	Intermediate Similarity	NPC305475
0.747	Intermediate Similarity	NPC82488
0.747	Intermediate Similarity	NPC475210
0.747	Intermediate Similarity	NPC98557
0.747	Intermediate Similarity	NPC308545
0.747	Intermediate Similarity	NPC99651
0.747	Intermediate Similarity	NPC167881
0.747	Intermediate Similarity	NPC164308
0.7468	Intermediate Similarity	NPC320119
0.7467	Intermediate Similarity	NPC68343
0.7467	Intermediate Similarity	NPC328089
0.7444	Intermediate Similarity	NPC12172
0.7444	Intermediate Similarity	NPC208886
0.7442	Intermediate Similarity	NPC295799
0.7442	Intermediate Similarity	NPC70424
0.7442	Intermediate Similarity	NPC165287
0.7442	Intermediate Similarity	NPC114979
0.7442	Intermediate Similarity	NPC243618
0.7442	Intermediate Similarity	NPC141193
0.7442	Intermediate Similarity	NPC474776
0.7442	Intermediate Similarity	NPC476804
0.7442	Intermediate Similarity	NPC96259
0.7442	Intermediate Similarity	NPC191476
0.7439	Intermediate Similarity	NPC240170
0.7439	Intermediate Similarity	NPC120776
0.7432	Intermediate Similarity	NPC321838
0.7423	Intermediate Similarity	NPC478038
0.7416	Intermediate Similarity	NPC97577
0.7416	Intermediate Similarity	NPC256902
0.7416	Intermediate Similarity	NPC474032
0.7416	Intermediate Similarity	NPC118193
0.7412	Intermediate Similarity	NPC475690
0.7407	Intermediate Similarity	NPC255060
0.7407	Intermediate Similarity	NPC228411
0.7403	Intermediate Similarity	NPC26500
0.7403	Intermediate Similarity	NPC99619
0.7397	Intermediate Similarity	NPC470363
0.7396	Intermediate Similarity	NPC474165
0.7396	Intermediate Similarity	NPC475945
0.7396	Intermediate Similarity	NPC69171
0.7396	Intermediate Similarity	NPC475871
0.7396	Intermediate Similarity	NPC110989

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 NPC11796 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1786
0.2-0.3	3953
0.3-0.4	2166
0.4-0.5	609
0.5-0.6	395
0.6-0.7	67
0.7-0.8	20
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8148	Intermediate Similarity	NPD5369	Approved
0.7841	Intermediate Similarity	NPD7983	Approved
0.7831	Intermediate Similarity	NPD6435	Approved
0.7831	Intermediate Similarity	NPD4269	Approved
0.7831	Intermediate Similarity	NPD4270	Approved
0.7738	Intermediate Similarity	NPD7154	Phase 3
0.7703	Intermediate Similarity	NPD3197	Phase 1
0.7674	Intermediate Similarity	NPD5786	Approved
0.759	Intermediate Similarity	NPD5368	Approved
0.759	Intermediate Similarity	NPD4252	Approved
0.7558	Intermediate Similarity	NPD5363	Approved
0.7416	Intermediate Similarity	NPD6101	Approved
0.7416	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD46	Approved
0.7333	Intermediate Similarity	NPD6698	Approved
0.7333	Intermediate Similarity	NPD5785	Approved
0.7326	Intermediate Similarity	NPD5362	Discontinued
0.7253	Intermediate Similarity	NPD6411	Approved
0.7204	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4822	Approved
0.7176	Intermediate Similarity	NPD4821	Approved
0.7176	Intermediate Similarity	NPD4820	Approved
0.7176	Intermediate Similarity	NPD4819	Approved
0.7174	Intermediate Similarity	NPD5778	Approved
0.7174	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD4271	Approved
0.7143	Intermediate Similarity	NPD3732	Approved
0.7143	Intermediate Similarity	NPD4268	Approved
0.7033	Intermediate Similarity	NPD5370	Suspended
0.7	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4250	Approved
0.7	Intermediate Similarity	NPD4251	Approved
0.6979	Remote Similarity	NPD4225	Approved
0.6966	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7839	Suspended
0.6944	Remote Similarity	NPD3196	Approved
0.6944	Remote Similarity	NPD4266	Approved
0.6944	Remote Similarity	NPD3195	Phase 2
0.6944	Remote Similarity	NPD3194	Approved
0.6889	Remote Similarity	NPD4249	Approved
0.6882	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3172	Approved
0.68	Remote Similarity	NPD6109	Phase 1
0.6796	Remote Similarity	NPD6371	Approved
0.6778	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7838	Discovery
0.6742	Remote Similarity	NPD5332	Approved
0.6742	Remote Similarity	NPD5331	Approved
0.6737	Remote Similarity	NPD5282	Discontinued
0.6731	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3728	Approved
0.6712	Remote Similarity	NPD3730	Approved
0.6705	Remote Similarity	NPD4790	Discontinued
0.6702	Remote Similarity	NPD7637	Suspended
0.6632	Remote Similarity	NPD6399	Phase 3
0.6623	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD8039	Approved
0.6574	Remote Similarity	NPD7115	Discovery
0.6528	Remote Similarity	NPD28	Approved
0.6528	Remote Similarity	NPD29	Approved
0.6494	Remote Similarity	NPD3198	Approved
0.6486	Remote Similarity	NPD8513	Phase 3
0.6486	Remote Similarity	NPD8515	Approved
0.6486	Remote Similarity	NPD8516	Approved
0.6486	Remote Similarity	NPD8517	Approved
0.6442	Remote Similarity	NPD6686	Approved
0.642	Remote Similarity	NPD7331	Phase 2
0.6413	Remote Similarity	NPD1694	Approved
0.6375	Remote Similarity	NPD7909	Approved
0.6364	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD6083	Phase 2
0.6344	Remote Similarity	NPD7334	Approved
0.6344	Remote Similarity	NPD6422	Discontinued
0.6344	Remote Similarity	NPD7146	Approved
0.6344	Remote Similarity	NPD7521	Approved
0.6344	Remote Similarity	NPD5330	Approved
0.6344	Remote Similarity	NPD6684	Approved
0.6344	Remote Similarity	NPD6409	Approved
0.6316	Remote Similarity	NPD1695	Approved
0.6304	Remote Similarity	NPD4786	Approved
0.63	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5209	Approved
0.6264	Remote Similarity	NPD3667	Approved
0.6263	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3173	Approved
0.6224	Remote Similarity	NPD7748	Approved
0.6211	Remote Similarity	NPD6903	Approved
0.6211	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8074	Phase 3
0.6204	Remote Similarity	NPD8297	Approved
0.62	Remote Similarity	NPD7902	Approved
0.619	Remote Similarity	NPD6412	Phase 2
0.6186	Remote Similarity	NPD7515	Phase 2
0.617	Remote Similarity	NPD3618	Phase 1
0.6162	Remote Similarity	NPD5695	Phase 3
0.6145	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5696	Approved
0.6136	Remote Similarity	NPD819	Approved
0.6136	Remote Similarity	NPD818	Approved
0.6132	Remote Similarity	NPD6881	Approved
0.6132	Remote Similarity	NPD6899	Approved
0.6129	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3133	Approved
0.6129	Remote Similarity	NPD3666	Approved
0.6129	Remote Similarity	NPD3665	Phase 1
0.6111	Remote Similarity	NPD5343	Approved
0.6111	Remote Similarity	NPD6649	Approved
0.6111	Remote Similarity	NPD622	Approved
0.6111	Remote Similarity	NPD6650	Approved
0.6106	Remote Similarity	NPD6319	Approved
0.61	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7341	Phase 2
0.6098	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5739	Approved
0.6095	Remote Similarity	NPD6675	Approved
0.6095	Remote Similarity	NPD6402	Approved
0.6095	Remote Similarity	NPD7128	Approved
0.6087	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6373	Approved
0.6075	Remote Similarity	NPD6372	Approved
0.6071	Remote Similarity	NPD7641	Discontinued
0.6064	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD8444	Approved
0.6042	Remote Similarity	NPD6672	Approved
0.6042	Remote Similarity	NPD5737	Approved
0.6038	Remote Similarity	NPD5697	Approved
0.6034	Remote Similarity	NPD8340	Approved
0.6034	Remote Similarity	NPD8341	Approved
0.6034	Remote Similarity	NPD8299	Approved
0.6034	Remote Similarity	NPD8342	Approved
0.6034	Remote Similarity	NPD7492	Approved
0.6022	Remote Similarity	NPD6110	Phase 1
0.602	Remote Similarity	NPD8035	Phase 2
0.602	Remote Similarity	NPD8034	Phase 2
0.602	Remote Similarity	NPD6079	Approved
0.6019	Remote Similarity	NPD7102	Approved
0.6019	Remote Similarity	NPD7290	Approved
0.6019	Remote Similarity	NPD6421	Discontinued
0.6019	Remote Similarity	NPD5344	Discontinued
0.6019	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD4802	Phase 2
0.6	Remote Similarity	NPD4238	Approved
0.5983	Remote Similarity	NPD6616	Approved
0.5983	Remote Similarity	NPD8451	Approved
0.5981	Remote Similarity	NPD7320	Approved
0.598	Remote Similarity	NPD7638	Approved
0.5979	Remote Similarity	NPD5328	Approved
0.5965	Remote Similarity	NPD6054	Approved
0.5963	Remote Similarity	NPD6869	Approved
0.5963	Remote Similarity	NPD8130	Phase 1
0.5963	Remote Similarity	NPD6617	Approved
0.5963	Remote Similarity	NPD1719	Phase 1
0.5963	Remote Similarity	NPD6847	Approved
0.5957	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD6933	Approved
0.5948	Remote Similarity	NPD7642	Approved
0.5948	Remote Similarity	NPD8328	Phase 3
0.5948	Remote Similarity	NPD7829	Approved
0.5948	Remote Similarity	NPD7830	Approved
0.5938	Remote Similarity	NPD7524	Approved
0.5932	Remote Similarity	NPD8448	Approved
0.5932	Remote Similarity	NPD7078	Approved
0.5926	Remote Similarity	NPD6014	Approved
0.5926	Remote Similarity	NPD6012	Approved
0.5926	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6013	Approved
0.5922	Remote Similarity	NPD7640	Approved
0.5922	Remote Similarity	NPD7639	Approved
0.5918	Remote Similarity	NPD5207	Approved
0.5909	Remote Similarity	NPD6882	Approved
0.59	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.59	Remote Similarity	NPD7900	Approved
0.589	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5701	Approved
0.5888	Remote Similarity	NPD6685	Approved
0.5882	Remote Similarity	NPD7736	Approved
0.587	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6370	Approved
0.5859	Remote Similarity	NPD5284	Approved
0.5859	Remote Similarity	NPD5281	Approved
0.5856	Remote Similarity	NPD4632	Approved
0.5847	Remote Similarity	NPD8273	Phase 1
0.5842	Remote Similarity	NPD4629	Approved
0.5842	Remote Similarity	NPD5210	Approved
0.5842	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD39	Approved
0.5833	Remote Similarity	NPD6011	Approved
0.5833	Remote Similarity	NPD634	Phase 3
0.5833	Remote Similarity	NPD6098	Approved
0.5833	Remote Similarity	NPD3174	Discontinued
0.5833	Remote Similarity	NPD4222	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