NPASS Compound

Structure

NPC126691 OpenBabel07101719152D 26 30 0 0 1 0 0 0 0 0999 V2000 -3.2409 1.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8813 -1.3668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5350 -1.7852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3593 -0.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1628 -0.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6575 0.5965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6046 -0.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3254 -0.9669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1751 1.6656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5684 0.7823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7866 1.7667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1628 0.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3549 0.9844 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4880 0.4835 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5684 -0.7823 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2746 2.2502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2746 1.2832 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4880 -0.4835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9616 0.1011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0002 0.9669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2696 -1.7019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0568 2.8185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8374 -0.4835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3549 2.5490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3254 0.9669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 19 1 0 0 0 0 4 6 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 5 12 1 0 0 0 0 6 17 1 0 0 0 0 7 19 1 0 0 0 0 8 18 1 0 0 0 0 9 10 2 0 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 9 1 6 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 21 2 0 0 0 0 12 26 1 0 0 0 0 13 17 1 6 0 0 0 13 19 1 0 0 0 0 14 18 1 6 0 0 0 14 26 1 0 0 0 0 15 18 1 6 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 1 1 1 0 0 0 18 2 1 1 0 0 0 19 20 1 1 0 0 0 20 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	356.526
LogP:	2.307
LogD:	2.128
LogS:	-4.547
# Rotatable Bonds:	0
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.501
Synthetic Accessibility Score:	5.206
Fsp3:	0.8
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:	-5.339
MDCK Permeability:	1.4008384823682718e-05
Pgp-inhibitor:	0.903
Pgp-substrate:	0.671
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.283
30% Bioavailability (F30%):	0.625

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.748
Plasma Protein Binding (PPB):	50.877471923828125%
Volume Distribution (VD):	0.848
Pgp-substrate:	41.33845138549805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.777
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.584
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.33

ADMET: Excretion

Clearance (CL):	2.133
Half-life (T1/2):	0.529

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.695
Drug-inuced Liver Injury (DILI):	0.219
AMES Toxicity:	0.649
Rat Oral Acute Toxicity:	0.982
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.328
Carcinogencity:	0.308
Eye Corrosion:	0.006
Eye Irritation:	0.024
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC126691

Natural Product ID:	NPC126691
*Common Name:**	Geniculol
IUPAC Name:	n.a.
Synonyms:	Geniculol
Standard InCHIKey:	JMAPMWNXFJANPJ-OTLMSYBKSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-17-6-4-7-19(3)13(17)11(25-16(17)23)9-10-14-18(2,8-5-12(21)26-14)15(22)20(10,19)24/h9,11,13-15,22,24H,4-8H2,1-3H3/t11-,13+,14+,15+,17+,18+,19+,20-/m1/s1
SMILES:	O=C1CC[C@]2([C@@H](O1)C1=C[C@H]3OC(=O)[C@@]4([C@H]3[C@]([C@@]1([C@H]2O)O)(C)CCC4)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452485
PubChem CID:	10713668
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO32658	geniculosporium sp.	Species	Xylariaceae	Eukaryota	n.a.	isolated from the marine red alga Polysiphonia	n.a.	PMID[15787444]
NPO32658	geniculosporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917307]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	2.0	mm	PMID[468084]

☑ 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 NPC126691 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	219
0.1-0.2	1245
0.2-0.3	4068
0.3-0.4	8496
0.4-0.5	12875
0.5-0.6	6187
0.6-0.7	7017
0.7-0.8	2491
0.8-0.85	90
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8857	High Similarity	NPC474775
0.8774	High Similarity	NPC258532
0.8611	High Similarity	NPC59530
0.8545	High Similarity	NPC5103
0.8522	High Similarity	NPC79579
0.8522	High Similarity	NPC474585
0.8496	Intermediate Similarity	NPC266728
0.8496	Intermediate Similarity	NPC49492
0.8482	Intermediate Similarity	NPC312017
0.8482	Intermediate Similarity	NPC9848
0.8435	Intermediate Similarity	NPC475041
0.8421	Intermediate Similarity	NPC470171
0.8407	Intermediate Similarity	NPC326542
0.8376	Intermediate Similarity	NPC222688
0.8376	Intermediate Similarity	NPC107493
0.8348	Intermediate Similarity	NPC153440
0.8333	Intermediate Similarity	NPC36688
0.8333	Intermediate Similarity	NPC138372
0.8333	Intermediate Similarity	NPC106228
0.8333	Intermediate Similarity	NPC140723
0.8319	Intermediate Similarity	NPC962
0.8319	Intermediate Similarity	NPC469454
0.8319	Intermediate Similarity	NPC469496
0.8319	Intermediate Similarity	NPC469463
0.8318	Intermediate Similarity	NPC39683
0.8304	Intermediate Similarity	NPC179798
0.8304	Intermediate Similarity	NPC304180
0.8291	Intermediate Similarity	NPC46570
0.8288	Intermediate Similarity	NPC472534
0.8288	Intermediate Similarity	NPC143706
0.8276	Intermediate Similarity	NPC305260
0.8276	Intermediate Similarity	NPC5292
0.8276	Intermediate Similarity	NPC270850
0.8273	Intermediate Similarity	NPC144459
0.8273	Intermediate Similarity	NPC475781
0.8273	Intermediate Similarity	NPC230541
0.8261	Intermediate Similarity	NPC473590
0.8257	Intermediate Similarity	NPC296950
0.8257	Intermediate Similarity	NPC471293
0.8257	Intermediate Similarity	NPC146731
0.8246	Intermediate Similarity	NPC178289
0.8246	Intermediate Similarity	NPC474181
0.8246	Intermediate Similarity	NPC117712
0.823	Intermediate Similarity	NPC207251
0.823	Intermediate Similarity	NPC269530
0.8224	Intermediate Similarity	NPC218383
0.822	Intermediate Similarity	NPC269642
0.8214	Intermediate Similarity	NPC50223
0.8214	Intermediate Similarity	NPC42776
0.8214	Intermediate Similarity	NPC206595
0.8214	Intermediate Similarity	NPC41551
0.8205	Intermediate Similarity	NPC109973
0.8198	Intermediate Similarity	NPC472217
0.8198	Intermediate Similarity	NPC472218
0.8198	Intermediate Similarity	NPC472219
0.8182	Intermediate Similarity	NPC469607
0.8174	Intermediate Similarity	NPC190286
0.8174	Intermediate Similarity	NPC474734
0.8174	Intermediate Similarity	NPC196931
0.8165	Intermediate Similarity	NPC26478
0.8165	Intermediate Similarity	NPC260809
0.8165	Intermediate Similarity	NPC474783
0.8158	Intermediate Similarity	NPC56448
0.8158	Intermediate Similarity	NPC250109
0.8158	Intermediate Similarity	NPC194100
0.8148	Intermediate Similarity	NPC474327
0.8136	Intermediate Similarity	NPC471999
0.8136	Intermediate Similarity	NPC472000
0.8131	Intermediate Similarity	NPC23364
0.8125	Intermediate Similarity	NPC173905
0.8125	Intermediate Similarity	NPC5475
0.8125	Intermediate Similarity	NPC141350
0.8125	Intermediate Similarity	NPC472216
0.8125	Intermediate Similarity	NPC284828
0.812	Intermediate Similarity	NPC19028
0.812	Intermediate Similarity	NPC477071
0.812	Intermediate Similarity	NPC9674
0.8103	Intermediate Similarity	NPC473968
0.8103	Intermediate Similarity	NPC469684
0.8103	Intermediate Similarity	NPC176513
0.8103	Intermediate Similarity	NPC470775
0.8099	Intermediate Similarity	NPC473265
0.8095	Intermediate Similarity	NPC250075
0.8091	Intermediate Similarity	NPC477812
0.8091	Intermediate Similarity	NPC75531
0.8091	Intermediate Similarity	NPC149124
0.8087	Intermediate Similarity	NPC265290
0.8087	Intermediate Similarity	NPC123117
0.8087	Intermediate Similarity	NPC305044
0.8083	Intermediate Similarity	NPC8369
0.8073	Intermediate Similarity	NPC214714
0.8073	Intermediate Similarity	NPC200672
0.8073	Intermediate Similarity	NPC252242
0.8073	Intermediate Similarity	NPC475956
0.8073	Intermediate Similarity	NPC185530
0.8073	Intermediate Similarity	NPC295791
0.807	Intermediate Similarity	NPC472002
0.807	Intermediate Similarity	NPC236217
0.807	Intermediate Similarity	NPC302146
0.807	Intermediate Similarity	NPC280782
0.8053	Intermediate Similarity	NPC235014
0.8051	Intermediate Similarity	NPC472004
0.8037	Intermediate Similarity	NPC182811
0.8037	Intermediate Similarity	NPC475894
0.8036	Intermediate Similarity	NPC329417
0.8036	Intermediate Similarity	NPC189075
0.8036	Intermediate Similarity	NPC275539
0.8036	Intermediate Similarity	NPC472825
0.8034	Intermediate Similarity	NPC470776
0.8033	Intermediate Similarity	NPC473888
0.8033	Intermediate Similarity	NPC311534
0.8018	Intermediate Similarity	NPC127609
0.8017	Intermediate Similarity	NPC474046
0.8017	Intermediate Similarity	NPC176840
0.8017	Intermediate Similarity	NPC259306
0.8017	Intermediate Similarity	NPC470628
0.8017	Intermediate Similarity	NPC179626
0.8017	Intermediate Similarity	NPC148458
0.8	Intermediate Similarity	NPC293658
0.8	Intermediate Similarity	NPC317210
0.8	Intermediate Similarity	NPC236390
0.8	Intermediate Similarity	NPC474410
0.8	Intermediate Similarity	NPC67251
0.8	Intermediate Similarity	NPC25909
0.8	Intermediate Similarity	NPC27363
0.8	Intermediate Similarity	NPC469789
0.8	Intermediate Similarity	NPC473979
0.7983	Intermediate Similarity	NPC470921
0.7983	Intermediate Similarity	NPC472001
0.7982	Intermediate Similarity	NPC475480
0.7982	Intermediate Similarity	NPC472003
0.7982	Intermediate Similarity	NPC475668
0.7982	Intermediate Similarity	NPC474846
0.7982	Intermediate Similarity	NPC150923
0.7982	Intermediate Similarity	NPC56025
0.7982	Intermediate Similarity	NPC26557
0.7982	Intermediate Similarity	NPC474750
0.7982	Intermediate Similarity	NPC469655
0.7982	Intermediate Similarity	NPC469656
0.7982	Intermediate Similarity	NPC94650
0.7982	Intermediate Similarity	NPC473921
0.7982	Intermediate Similarity	NPC188738
0.7982	Intermediate Similarity	NPC81530
0.7967	Intermediate Similarity	NPC231529
0.7967	Intermediate Similarity	NPC470880
0.7966	Intermediate Similarity	NPC122971
0.7963	Intermediate Similarity	NPC216478
0.7963	Intermediate Similarity	NPC474957
0.7963	Intermediate Similarity	NPC271387
0.7963	Intermediate Similarity	NPC153792
0.7963	Intermediate Similarity	NPC274458
0.7963	Intermediate Similarity	NPC79449
0.7951	Intermediate Similarity	NPC287423
0.7951	Intermediate Similarity	NPC470882
0.7951	Intermediate Similarity	NPC473253
0.7949	Intermediate Similarity	NPC98249
0.7949	Intermediate Similarity	NPC23046
0.7949	Intermediate Similarity	NPC53396
0.7946	Intermediate Similarity	NPC220229
0.7946	Intermediate Similarity	NPC110496
0.7946	Intermediate Similarity	NPC64844
0.7946	Intermediate Similarity	NPC475060
0.7946	Intermediate Similarity	NPC42847
0.7946	Intermediate Similarity	NPC67321
0.7946	Intermediate Similarity	NPC83744
0.7946	Intermediate Similarity	NPC255387
0.7946	Intermediate Similarity	NPC131665
0.7946	Intermediate Similarity	NPC112780
0.7946	Intermediate Similarity	NPC187435
0.7931	Intermediate Similarity	NPC181145
0.7931	Intermediate Similarity	NPC469877
0.7931	Intermediate Similarity	NPC470919
0.7931	Intermediate Similarity	NPC471398
0.7931	Intermediate Similarity	NPC243354
0.7931	Intermediate Similarity	NPC473898
0.7928	Intermediate Similarity	NPC470104
0.7928	Intermediate Similarity	NPC152966
0.792	Intermediate Similarity	NPC157817
0.792	Intermediate Similarity	NPC225385
0.792	Intermediate Similarity	NPC104585
0.792	Intermediate Similarity	NPC298783
0.7917	Intermediate Similarity	NPC473231
0.7913	Intermediate Similarity	NPC40608
0.7909	Intermediate Similarity	NPC195290
0.7909	Intermediate Similarity	NPC469606
0.7909	Intermediate Similarity	NPC31058
0.7909	Intermediate Similarity	NPC273005
0.7909	Intermediate Similarity	NPC204450
0.7909	Intermediate Similarity	NPC473928
0.7909	Intermediate Similarity	NPC136289
0.7909	Intermediate Similarity	NPC235369
0.7909	Intermediate Similarity	NPC475986
0.7909	Intermediate Similarity	NPC170615
0.7903	Intermediate Similarity	NPC173347
0.7899	Intermediate Similarity	NPC143755
0.7899	Intermediate Similarity	NPC476961
0.7895	Intermediate Similarity	NPC124053
0.7895	Intermediate Similarity	NPC478211
0.7895	Intermediate Similarity	NPC76084
0.7895	Intermediate Similarity	NPC37116

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 NPC126691 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1437
0.2-0.3	3810
0.3-0.4	2487
0.4-0.5	707
0.5-0.6	226
0.6-0.7	220
0.7-0.8	80
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
0.807	Intermediate Similarity	NPD6053	Discontinued
0.7869	Intermediate Similarity	NPD7507	Approved
0.7857	Intermediate Similarity	NPD6008	Approved
0.768	Intermediate Similarity	NPD7319	Approved
0.7603	Intermediate Similarity	NPD6319	Approved
0.7568	Intermediate Similarity	NPD7639	Approved
0.7568	Intermediate Similarity	NPD7640	Approved
0.7565	Intermediate Similarity	NPD7320	Approved
0.7544	Intermediate Similarity	NPD5739	Approved
0.7544	Intermediate Similarity	NPD6675	Approved
0.7544	Intermediate Similarity	NPD7128	Approved
0.7544	Intermediate Similarity	NPD6402	Approved
0.7542	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD6372	Approved
0.7478	Intermediate Similarity	NPD5701	Approved
0.7478	Intermediate Similarity	NPD5697	Approved
0.7477	Intermediate Similarity	NPD7638	Approved
0.7459	Intermediate Similarity	NPD6059	Approved
0.7459	Intermediate Similarity	NPD6054	Approved
0.744	Intermediate Similarity	NPD6616	Approved
0.7414	Intermediate Similarity	NPD6686	Approved
0.7414	Intermediate Similarity	NPD6881	Approved
0.7414	Intermediate Similarity	NPD6899	Approved
0.7398	Intermediate Similarity	NPD8033	Approved
0.7398	Intermediate Similarity	NPD6016	Approved
0.7398	Intermediate Similarity	NPD6015	Approved
0.7381	Intermediate Similarity	NPD7078	Approved
0.7381	Intermediate Similarity	NPD8293	Discontinued
0.7373	Intermediate Similarity	NPD6650	Approved
0.7373	Intermediate Similarity	NPD6649	Approved
0.735	Intermediate Similarity	NPD6012	Approved
0.735	Intermediate Similarity	NPD6013	Approved
0.735	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6399	Phase 3
0.7339	Intermediate Similarity	NPD5988	Approved
0.7339	Intermediate Similarity	NPD6370	Approved
0.7328	Intermediate Similarity	NPD6412	Phase 2
0.7323	Intermediate Similarity	NPD7736	Approved
0.7321	Intermediate Similarity	NPD4225	Approved
0.7311	Intermediate Similarity	NPD8297	Approved
0.7295	Intermediate Similarity	NPD7328	Approved
0.7295	Intermediate Similarity	NPD7327	Approved
0.7288	Intermediate Similarity	NPD7102	Approved
0.7288	Intermediate Similarity	NPD4634	Approved
0.7288	Intermediate Similarity	NPD6371	Approved
0.7288	Intermediate Similarity	NPD6883	Approved
0.7288	Intermediate Similarity	NPD7290	Approved
0.7281	Intermediate Similarity	NPD5211	Phase 2
0.7265	Intermediate Similarity	NPD6011	Approved
0.7265	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8517	Approved
0.7258	Intermediate Similarity	NPD8516	Approved
0.7258	Intermediate Similarity	NPD8513	Phase 3
0.7258	Intermediate Similarity	NPD8515	Approved
0.7236	Intermediate Similarity	NPD7516	Approved
0.7232	Intermediate Similarity	NPD6083	Phase 2
0.7232	Intermediate Similarity	NPD6084	Phase 2
0.7232	Intermediate Similarity	NPD4755	Approved
0.7227	Intermediate Similarity	NPD6869	Approved
0.7227	Intermediate Similarity	NPD8130	Phase 1
0.7227	Intermediate Similarity	NPD6847	Approved
0.7227	Intermediate Similarity	NPD6617	Approved
0.7213	Intermediate Similarity	NPD6009	Approved
0.7207	Intermediate Similarity	NPD5695	Phase 3
0.7177	Intermediate Similarity	NPD8377	Approved
0.7177	Intermediate Similarity	NPD8294	Approved
0.7168	Intermediate Similarity	NPD5696	Approved
0.7167	Intermediate Similarity	NPD6882	Approved
0.7155	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7503	Approved
0.712	Intermediate Similarity	NPD8380	Approved
0.712	Intermediate Similarity	NPD8379	Approved
0.712	Intermediate Similarity	NPD5983	Phase 2
0.712	Intermediate Similarity	NPD8335	Approved
0.712	Intermediate Similarity	NPD8378	Approved
0.712	Intermediate Similarity	NPD8296	Approved
0.7107	Intermediate Similarity	NPD8133	Approved
0.7105	Intermediate Similarity	NPD5285	Approved
0.7105	Intermediate Similarity	NPD4700	Approved
0.7105	Intermediate Similarity	NPD5286	Approved
0.7105	Intermediate Similarity	NPD4696	Approved
0.7103	Intermediate Similarity	NPD4249	Approved
0.7083	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4251	Approved
0.7037	Intermediate Similarity	NPD4250	Approved
0.7034	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5779	Approved
0.7027	Intermediate Similarity	NPD5778	Approved
0.7008	Intermediate Similarity	NPD7604	Phase 2
0.7	Intermediate Similarity	NPD6698	Approved
0.7	Intermediate Similarity	NPD46	Approved
0.6992	Remote Similarity	NPD6274	Approved
0.6984	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5226	Approved
0.6983	Remote Similarity	NPD5225	Approved
0.6983	Remote Similarity	NPD7632	Discontinued
0.6983	Remote Similarity	NPD4633	Approved
0.6983	Remote Similarity	NPD5224	Approved
0.6977	Remote Similarity	NPD8074	Phase 3
0.6937	Remote Similarity	NPD5693	Phase 1
0.6937	Remote Similarity	NPD5281	Approved
0.6937	Remote Similarity	NPD6411	Approved
0.6937	Remote Similarity	NPD5284	Approved
0.6923	Remote Similarity	NPD5175	Approved
0.6923	Remote Similarity	NPD5174	Approved
0.6923	Remote Similarity	NPD6033	Approved
0.6909	Remote Similarity	NPD4753	Phase 2
0.6909	Remote Similarity	NPD6051	Approved
0.6903	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6336	Discontinued
0.6897	Remote Similarity	NPD5223	Approved
0.6891	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4202	Approved
0.6847	Remote Similarity	NPD5207	Approved
0.6825	Remote Similarity	NPD7100	Approved
0.6825	Remote Similarity	NPD7101	Approved
0.6822	Remote Similarity	NPD5362	Discontinued
0.6818	Remote Similarity	NPD6903	Approved
0.6814	Remote Similarity	NPD6001	Approved
0.6807	Remote Similarity	NPD4768	Approved
0.6807	Remote Similarity	NPD4767	Approved
0.68	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6317	Approved
0.6789	Remote Similarity	NPD6684	Approved
0.6789	Remote Similarity	NPD6409	Approved
0.6789	Remote Similarity	NPD7521	Approved
0.6789	Remote Similarity	NPD7334	Approved
0.6789	Remote Similarity	NPD5330	Approved
0.6789	Remote Similarity	NPD7146	Approved
0.6786	Remote Similarity	NPD7983	Approved
0.6786	Remote Similarity	NPD7637	Suspended
0.678	Remote Similarity	NPD4754	Approved
0.6777	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7260	Phase 2
0.6759	Remote Similarity	NPD4786	Approved
0.6759	Remote Similarity	NPD3133	Approved
0.6759	Remote Similarity	NPD3666	Approved
0.6759	Remote Similarity	NPD3665	Phase 1
0.6757	Remote Similarity	NPD6101	Approved
0.6757	Remote Similarity	NPD5328	Approved
0.6757	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1695	Approved
0.6754	Remote Similarity	NPD5210	Approved
0.6754	Remote Similarity	NPD4629	Approved
0.6746	Remote Similarity	NPD6314	Approved
0.6746	Remote Similarity	NPD6335	Approved
0.6746	Remote Similarity	NPD6313	Approved
0.6744	Remote Similarity	NPD8328	Phase 3
0.6729	Remote Similarity	NPD3667	Approved
0.6729	Remote Similarity	NPD6435	Approved
0.6727	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6909	Approved
0.6719	Remote Similarity	NPD6908	Approved
0.6716	Remote Similarity	NPD6845	Suspended
0.6698	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4822	Approved
0.6698	Remote Similarity	NPD4819	Approved
0.6698	Remote Similarity	NPD4821	Approved
0.6698	Remote Similarity	NPD4820	Approved
0.6697	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD1694	Approved
0.6696	Remote Similarity	NPD4697	Phase 3
0.6696	Remote Similarity	NPD5785	Approved
0.6694	Remote Similarity	NPD4730	Approved
0.6694	Remote Similarity	NPD4729	Approved
0.6694	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7902	Approved
0.6637	Remote Similarity	NPD8035	Phase 2
0.6637	Remote Similarity	NPD6079	Approved
0.6637	Remote Similarity	NPD8034	Phase 2
0.6636	Remote Similarity	NPD6098	Approved
0.6636	Remote Similarity	NPD3618	Phase 1
0.6636	Remote Similarity	NPD5786	Approved
0.6615	Remote Similarity	NPD6067	Discontinued
0.661	Remote Similarity	NPD5344	Discontinued
0.6607	Remote Similarity	NPD6904	Approved
0.6607	Remote Similarity	NPD6673	Approved
0.6607	Remote Similarity	NPD6080	Approved
0.6606	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD6921	Approved
0.6585	Remote Similarity	NPD5247	Approved
0.6585	Remote Similarity	NPD5249	Phase 3
0.6585	Remote Similarity	NPD5250	Approved
0.6585	Remote Similarity	NPD5251	Approved
0.6585	Remote Similarity	NPD5248	Approved
0.6577	Remote Similarity	NPD7524	Approved
0.6574	Remote Similarity	NPD4223	Phase 3
0.6574	Remote Similarity	NPD4221	Approved
0.6574	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD5956	Approved
0.6552	Remote Similarity	NPD5221	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