NPASS Compound

Structure

NPC86030 OpenBabel07101718292D 25 27 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 -1.7321 1.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -0.8660 -1.5000 0.0000 C 0 0 2 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 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 23 1 0 0 0 0 2 3 1 0 0 0 0 2 8 1 0 0 0 0 3 12 1 0 0 0 0 4 7 2 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 21 1 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 11 1 6 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 13 1 1 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.14
Volume:	348.433
LogP:	1.894
LogD:	2.204
LogS:	-3.531
# Rotatable Bonds:	6
TPSA:	88.38
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	3.104
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.159
MDCK Permeability:	1.1382488082745112e-05
Pgp-inhibitor:	0.66
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.631
Plasma Protein Binding (PPB):	91.83678436279297%
Volume Distribution (VD):	0.733
Pgp-substrate:	4.348283290863037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.222
CYP1A2-substrate:	0.514
CYP2C19-inhibitor:	0.296
CYP2C19-substrate:	0.415
CYP2C9-inhibitor:	0.608
CYP2C9-substrate:	0.696
CYP2D6-inhibitor:	0.629
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.85
CYP3A4-substrate:	0.645

ADMET: Excretion

Clearance (CL):	8.236
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.216
Drug-inuced Liver Injury (DILI):	0.305
AMES Toxicity:	0.417
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.364
Carcinogencity:	0.692
Eye Corrosion:	0.003
Eye Irritation:	0.06
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC86030

Natural Product ID:	NPC86030
*Common Name:**	Rel-(7Alpha,8Beta)-3-Methoxy-4',7-Epoxy-8,3'-Oxyneolignan-4,9,9'-Triol
IUPAC Name:	4-[(2R,3R)-3-(hydroxymethyl)-6-(3-hydroxypropyl)-2,3-dihydro-1,4-benzodioxin-2-yl]-2-methoxyphenol
Synonyms:
Standard InCHIKey:	CYLVTAFKOSKXKE-RTBURBONSA-N
Standard InCHI:	InChI=1S/C19H22O6/c1-23-16-10-13(5-6-14(16)22)19-18(11-21)24-17-9-12(3-2-8-20)4-7-15(17)25-19/h4-7,9-10,18-22H,2-3,8,11H2,1H3/t18-,19-/m1/s1
SMILES:	COc1cc(ccc1O)[C@@H]1[C@@H](CO)Oc2cc(CCCO)ccc2O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3088128
PubChem CID:	76317135
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002699] Benzodioxanes [CHEMONTID:0002704] Phenylbenzodioxanes [CHEMONTID:0002707] Phenylbenzo-1,4-dioxanes

*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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	30000.0	nM	PMID[509482]

☑ 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 NPC86030 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	383
0.1-0.2	1500
0.2-0.3	4696
0.3-0.4	12254
0.4-0.5	5743
0.5-0.6	4393
0.6-0.7	7674
0.7-0.8	4447
0.8-0.85	916
0.85-0.9	477
0.9-0.95	189
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC5851
0.9918	High Similarity	NPC72529
0.9836	High Similarity	NPC183181
0.9836	High Similarity	NPC292056
0.9836	High Similarity	NPC111247
0.9836	High Similarity	NPC147821
0.9836	High Similarity	NPC319625
0.9836	High Similarity	NPC118787
0.9836	High Similarity	NPC41706
0.9836	High Similarity	NPC163332
0.9756	High Similarity	NPC252307
0.9756	High Similarity	NPC245826
0.9756	High Similarity	NPC474178
0.9754	High Similarity	NPC191037
0.9754	High Similarity	NPC178284
0.9754	High Similarity	NPC58607
0.9672	High Similarity	NPC194519
0.9606	High Similarity	NPC170694
0.959	High Similarity	NPC114901
0.959	High Similarity	NPC94276
0.959	High Similarity	NPC293701
0.959	High Similarity	NPC48990
0.959	High Similarity	NPC109822
0.9524	High Similarity	NPC472597
0.9457	High Similarity	NPC16435
0.9457	High Similarity	NPC306441
0.9453	High Similarity	NPC478085
0.9449	High Similarity	NPC184447
0.9449	High Similarity	NPC160991
0.9449	High Similarity	NPC201587
0.9449	High Similarity	NPC16208
0.9449	High Similarity	NPC35932
0.9449	High Similarity	NPC253105
0.9449	High Similarity	NPC7903
0.9444	High Similarity	NPC472338
0.9426	High Similarity	NPC71090
0.9385	High Similarity	NPC470413
0.9385	High Similarity	NPC126206
0.9385	High Similarity	NPC138738
0.938	High Similarity	NPC234333
0.938	High Similarity	NPC47398
0.938	High Similarity	NPC214729
0.938	High Similarity	NPC121812
0.938	High Similarity	NPC94750
0.938	High Similarity	NPC260898
0.938	High Similarity	NPC61946
0.938	High Similarity	NPC112939
0.938	High Similarity	NPC474206
0.938	High Similarity	NPC112246
0.938	High Similarity	NPC470356
0.9365	High Similarity	NPC222004
0.9365	High Similarity	NPC190629
0.9365	High Similarity	NPC202582
0.9365	High Similarity	NPC3439
0.9365	High Similarity	NPC470258
0.9365	High Similarity	NPC218856
0.9365	High Similarity	NPC210623
0.9365	High Similarity	NPC273295
0.9365	High Similarity	NPC226788
0.9365	High Similarity	NPC285339
0.936	High Similarity	NPC165045
0.936	High Similarity	NPC118533
0.935	High Similarity	NPC471693
0.9344	High Similarity	NPC470804
0.9308	High Similarity	NPC227503
0.9308	High Similarity	NPC302701
0.9308	High Similarity	NPC474639
0.9308	High Similarity	NPC230734
0.9308	High Similarity	NPC471664
0.9308	High Similarity	NPC269091
0.9308	High Similarity	NPC471665
0.9302	High Similarity	NPC249791
0.9302	High Similarity	NPC119060
0.9302	High Similarity	NPC237594
0.9302	High Similarity	NPC310854
0.9302	High Similarity	NPC476387
0.9297	High Similarity	NPC470752
0.9291	High Similarity	NPC42300
0.9291	High Similarity	NPC187998
0.9291	High Similarity	NPC153739
0.9291	High Similarity	NPC145305
0.9291	High Similarity	NPC257582
0.9291	High Similarity	NPC174495
0.9291	High Similarity	NPC92164
0.9291	High Similarity	NPC77040
0.9291	High Similarity	NPC64201
0.9291	High Similarity	NPC241522
0.9291	High Similarity	NPC242807
0.9237	High Similarity	NPC102904
0.9237	High Similarity	NPC176051
0.9237	High Similarity	NPC103976
0.9237	High Similarity	NPC474282
0.9237	High Similarity	NPC107551
0.9237	High Similarity	NPC326797
0.9237	High Similarity	NPC211549
0.9231	High Similarity	NPC472337
0.9231	High Similarity	NPC164787
0.9231	High Similarity	NPC151224
0.9225	High Similarity	NPC263064
0.9225	High Similarity	NPC11060
0.9225	High Similarity	NPC475840
0.9225	High Similarity	NPC229442
0.9225	High Similarity	NPC168059
0.9219	High Similarity	NPC277804
0.9219	High Similarity	NPC469613
0.9219	High Similarity	NPC470095
0.9219	High Similarity	NPC469625
0.9219	High Similarity	NPC309787
0.9219	High Similarity	NPC470096
0.9219	High Similarity	NPC30043
0.9213	High Similarity	NPC170844
0.9213	High Similarity	NPC476968
0.9213	High Similarity	NPC475875
0.9206	High Similarity	NPC210355
0.9206	High Similarity	NPC5428
0.9206	High Similarity	NPC474119
0.92	High Similarity	NPC148627
0.9187	High Similarity	NPC343720
0.9187	High Similarity	NPC473853
0.9187	High Similarity	NPC113865
0.9187	High Similarity	NPC290451
0.9187	High Similarity	NPC127389
0.9187	High Similarity	NPC312675
0.9187	High Similarity	NPC54872
0.9187	High Similarity	NPC184651
0.9187	High Similarity	NPC470212
0.9187	High Similarity	NPC324571
0.9187	High Similarity	NPC262156
0.918	High Similarity	NPC35071
0.918	High Similarity	NPC177475
0.918	High Similarity	NPC148615
0.9173	High Similarity	NPC471389
0.9173	High Similarity	NPC83375
0.9173	High Similarity	NPC224876
0.9167	High Similarity	NPC22517
0.916	High Similarity	NPC270456
0.916	High Similarity	NPC199459
0.916	High Similarity	NPC477939
0.916	High Similarity	NPC54743
0.916	High Similarity	NPC156502
0.916	High Similarity	NPC52277
0.916	High Similarity	NPC248727
0.916	High Similarity	NPC209985
0.916	High Similarity	NPC472334
0.916	High Similarity	NPC162659
0.916	High Similarity	NPC177035
0.916	High Similarity	NPC472336
0.916	High Similarity	NPC29799
0.916	High Similarity	NPC177160
0.916	High Similarity	NPC10737
0.916	High Similarity	NPC77861
0.916	High Similarity	NPC263367
0.916	High Similarity	NPC265433
0.916	High Similarity	NPC470802
0.9154	High Similarity	NPC187194
0.9154	High Similarity	NPC317380
0.9147	High Similarity	NPC86655
0.9147	High Similarity	NPC15658
0.9147	High Similarity	NPC185604
0.9147	High Similarity	NPC78770
0.9147	High Similarity	NPC202762
0.9147	High Similarity	NPC127624
0.9147	High Similarity	NPC61477
0.9147	High Similarity	NPC261619
0.9147	High Similarity	NPC126029
0.9147	High Similarity	NPC219876
0.9141	High Similarity	NPC469614
0.9141	High Similarity	NPC469612
0.9134	High Similarity	NPC129570
0.9134	High Similarity	NPC128208
0.9134	High Similarity	NPC470213
0.9134	High Similarity	NPC206615
0.9134	High Similarity	NPC98631
0.9134	High Similarity	NPC184733
0.9134	High Similarity	NPC282703
0.9134	High Similarity	NPC21867
0.9134	High Similarity	NPC470084
0.9134	High Similarity	NPC186843
0.9134	High Similarity	NPC45774
0.9134	High Similarity	NPC11258
0.9113	High Similarity	NPC209567
0.9106	High Similarity	NPC207613
0.9104	High Similarity	NPC189115
0.9104	High Similarity	NPC278469
0.9104	High Similarity	NPC476356
0.9104	High Similarity	NPC469559
0.9104	High Similarity	NPC193722
0.9098	High Similarity	NPC309124
0.9098	High Similarity	NPC184797
0.9098	High Similarity	NPC320987
0.9098	High Similarity	NPC55793
0.9098	High Similarity	NPC291101
0.9098	High Similarity	NPC266197
0.9098	High Similarity	NPC135961
0.9098	High Similarity	NPC181969
0.9098	High Similarity	NPC106944
0.9091	High Similarity	NPC276490
0.9091	High Similarity	NPC474390
0.9084	High Similarity	NPC473413
0.907	High Similarity	NPC27843

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 NPC86030 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	853
0.2-0.3	1864
0.3-0.4	2667
0.4-0.5	1641
0.5-0.6	892
0.6-0.7	701
0.7-0.8	188
0.8-0.85	8
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9213	High Similarity	NPD3027	Phase 3
0.9147	High Similarity	NPD1613	Approved
0.9147	High Similarity	NPD1612	Clinical (unspecified phase)
0.8837	High Similarity	NPD1529	Clinical (unspecified phase)
0.876	High Similarity	NPD1530	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD228	Approved
0.8333	Intermediate Similarity	NPD2861	Phase 2
0.8201	Intermediate Similarity	NPD7266	Discontinued
0.8168	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1934	Approved
0.8162	Intermediate Similarity	NPD1558	Phase 1
0.816	Intermediate Similarity	NPD5283	Phase 1
0.8134	Intermediate Similarity	NPD4908	Phase 1
0.8116	Intermediate Similarity	NPD4536	Approved
0.8116	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD4538	Approved
0.8085	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD2684	Approved
0.8029	Intermediate Similarity	NPD3620	Phase 2
0.8029	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1091	Approved
0.8015	Intermediate Similarity	NPD1610	Phase 2
0.8014	Intermediate Similarity	NPD1653	Approved
0.7987	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD1548	Phase 1
0.7958	Intermediate Similarity	NPD6674	Discontinued
0.7937	Intermediate Similarity	NPD7843	Approved
0.7929	Intermediate Similarity	NPD5588	Approved
0.7929	Intermediate Similarity	NPD5960	Phase 3
0.7895	Intermediate Similarity	NPD2982	Phase 2
0.7895	Intermediate Similarity	NPD2983	Phase 2
0.7891	Intermediate Similarity	NPD7157	Approved
0.7879	Intermediate Similarity	NPD3705	Approved
0.7871	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6166	Phase 2
0.7871	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2801	Approved
0.784	Intermediate Similarity	NPD3022	Approved
0.784	Intermediate Similarity	NPD3021	Approved
0.7832	Intermediate Similarity	NPD3060	Approved
0.7823	Intermediate Similarity	NPD290	Approved
0.782	Intermediate Similarity	NPD2981	Phase 2
0.7794	Intermediate Similarity	NPD3018	Phase 2
0.7793	Intermediate Similarity	NPD5058	Phase 3
0.7786	Intermediate Similarity	NPD1357	Approved
0.777	Intermediate Similarity	NPD4060	Phase 1
0.7763	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD6671	Approved
0.7742	Intermediate Similarity	NPD968	Approved
0.7727	Intermediate Similarity	NPD6516	Phase 2
0.7727	Intermediate Similarity	NPD5846	Approved
0.7722	Intermediate Similarity	NPD7054	Approved
0.7721	Intermediate Similarity	NPD6584	Phase 3
0.7708	Intermediate Similarity	NPD4236	Phase 3
0.7708	Intermediate Similarity	NPD4237	Approved
0.7708	Intermediate Similarity	NPD4162	Approved
0.7705	Intermediate Similarity	NPD291	Approved
0.7704	Intermediate Similarity	NPD8651	Approved
0.7698	Intermediate Similarity	NPD6233	Phase 2
0.7692	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD4123	Phase 3
0.7681	Intermediate Similarity	NPD4625	Phase 3
0.7673	Intermediate Similarity	NPD7074	Phase 3
0.7673	Intermediate Similarity	NPD7472	Approved
0.7647	Intermediate Similarity	NPD3882	Suspended
0.7634	Intermediate Similarity	NPD5536	Phase 2
0.763	Intermediate Similarity	NPD4749	Approved
0.7626	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1511	Approved
0.7609	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2677	Approved
0.7603	Intermediate Similarity	NPD6190	Approved
0.7589	Intermediate Similarity	NPD5735	Approved
0.7586	Intermediate Similarity	NPD5177	Phase 3
0.7556	Intermediate Similarity	NPD2231	Phase 2
0.7556	Intermediate Similarity	NPD2235	Phase 2
0.7554	Intermediate Similarity	NPD7095	Approved
0.755	Intermediate Similarity	NPD4675	Approved
0.755	Intermediate Similarity	NPD4678	Approved
0.7548	Intermediate Similarity	NPD6234	Discontinued
0.7547	Intermediate Similarity	NPD3818	Discontinued
0.7534	Intermediate Similarity	NPD6331	Phase 2
0.7534	Intermediate Similarity	NPD4535	Phase 3
0.7534	Intermediate Similarity	NPD4628	Phase 3
0.7533	Intermediate Similarity	NPD3686	Approved
0.7533	Intermediate Similarity	NPD3687	Approved
0.7517	Intermediate Similarity	NPD1512	Approved
0.7516	Intermediate Similarity	NPD6797	Phase 2
0.7516	Intermediate Similarity	NPD5772	Approved
0.7516	Intermediate Similarity	NPD2978	Approved
0.7516	Intermediate Similarity	NPD2977	Approved
0.7516	Intermediate Similarity	NPD5773	Approved
0.75	Intermediate Similarity	NPD1774	Approved
0.75	Intermediate Similarity	NPD6583	Phase 3
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6582	Phase 2
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7469	Intermediate Similarity	NPD7251	Discontinued
0.7468	Intermediate Similarity	NPD3817	Phase 2
0.7466	Intermediate Similarity	NPD1652	Phase 2
0.7465	Intermediate Similarity	NPD4340	Discontinued
0.7451	Intermediate Similarity	NPD37	Approved
0.7448	Intermediate Similarity	NPD1375	Discontinued
0.7447	Intermediate Similarity	NPD2674	Phase 3
0.7447	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7228	Approved
0.7431	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7808	Phase 3
0.7423	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4967	Phase 2
0.7419	Intermediate Similarity	NPD4965	Approved
0.7419	Intermediate Similarity	NPD4966	Approved
0.7415	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4110	Phase 3
0.7413	Intermediate Similarity	NPD6653	Approved
0.7403	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5844	Phase 1
0.7385	Intermediate Similarity	NPD5535	Approved
0.7376	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5241	Discontinued
0.7365	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2122	Discontinued
0.7343	Intermediate Similarity	NPD6355	Discontinued
0.7342	Intermediate Similarity	NPD7199	Phase 2
0.7329	Intermediate Similarity	NPD5762	Approved
0.7329	Intermediate Similarity	NPD5763	Approved
0.7324	Intermediate Similarity	NPD4062	Phase 3
0.732	Intermediate Similarity	NPD4380	Phase 2
0.7312	Intermediate Similarity	NPD27	Approved
0.7312	Intermediate Similarity	NPD2489	Approved
0.731	Intermediate Similarity	NPD7033	Discontinued
0.7305	Intermediate Similarity	NPD3179	Approved
0.7305	Intermediate Similarity	NPD3180	Approved
0.7301	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3054	Approved
0.7292	Intermediate Similarity	NPD3052	Approved
0.7286	Intermediate Similarity	NPD9494	Approved
0.7285	Intermediate Similarity	NPD7526	Approved
0.7285	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD52	Approved
0.7279	Intermediate Similarity	NPD2424	Discontinued
0.7279	Intermediate Similarity	NPD3496	Discontinued
0.7273	Intermediate Similarity	NPD4140	Approved
0.7273	Intermediate Similarity	NPD3061	Approved
0.7273	Intermediate Similarity	NPD3062	Approved
0.7273	Intermediate Similarity	NPD3059	Approved
0.7273	Intermediate Similarity	NPD2238	Phase 2
0.7267	Intermediate Similarity	NPD7213	Phase 3
0.7267	Intermediate Similarity	NPD7212	Phase 2
0.7266	Intermediate Similarity	NPD3094	Phase 2
0.7261	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2161	Phase 2
0.7256	Intermediate Similarity	NPD7685	Pre-registration
0.7255	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4005	Discontinued
0.7254	Intermediate Similarity	NPD3144	Approved
0.7254	Intermediate Similarity	NPD3145	Approved
0.7254	Intermediate Similarity	NPD5718	Phase 2
0.7252	Intermediate Similarity	NPD821	Approved
0.725	Intermediate Similarity	NPD2970	Approved
0.725	Intermediate Similarity	NPD2969	Approved
0.7246	Intermediate Similarity	NPD5327	Phase 3
0.7244	Intermediate Similarity	NPD2563	Approved
0.7244	Intermediate Similarity	NPD2560	Approved
0.7241	Intermediate Similarity	NPD7097	Phase 1
0.7226	Intermediate Similarity	NPD422	Phase 1
0.7222	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5124	Phase 1
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7447	Phase 1
0.7219	Intermediate Similarity	NPD3536	Discontinued
0.7219	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD2933	Approved
0.7213	Intermediate Similarity	NPD2934	Approved
0.7213	Intermediate Similarity	NPD9296	Approved
0.7211	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3540	Phase 1
0.7206	Intermediate Similarity	NPD9384	Approved
0.7206	Intermediate Similarity	NPD5125	Phase 3
0.7206	Intermediate Similarity	NPD9381	Approved
0.7206	Intermediate Similarity	NPD5126	Approved
0.7203	Intermediate Similarity	NPD3531	Approved
0.7203	Intermediate Similarity	NPD3532	Approved
0.7203	Intermediate Similarity	NPD3530	Approved
0.7188	Intermediate Similarity	NPD3051	Approved
0.7188	Intermediate Similarity	NPD6071	Discontinued
0.7185	Intermediate Similarity	NPD1182	Approved
0.7179	Intermediate Similarity	NPD1465	Phase 2
0.7179	Intermediate Similarity	NPD8455	Phase 2
0.7174	Intermediate Similarity	NPD1608	Approved
0.7172	Intermediate Similarity	NPD5314	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