NPASS Compound

Structure

NPC77878 OpenBabel07101718322D 26 30 0 0 0 0 0 0 0 0999 V2000 -0.6578 -5.3240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7407 -3.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3517 -2.9948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9886 -2.5605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -2.8950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1038 -4.0979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4093 -3.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3776 -2.5605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1785 -5.0951 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1594 -3.1840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5831 -4.3268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 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 24 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 20 1 0 0 0 0 5 10 2 0 0 0 0 5 11 1 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 25 1 0 0 0 0 7 26 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 20 2 0 0 0 0 16 22 2 0 0 0 0 17 19 2 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	351.07
Volume:	334.408
LogP:	3.084
LogD:	2.685
LogS:	-5.661
# Rotatable Bonds:	2
TPSA:	87.11
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.594
Synthetic Accessibility Score:	2.924
Fsp3:	0.158
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:	-4.813
MDCK Permeability:	1.69718678080244e-05
Pgp-inhibitor:	0.908
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	93.05914306640625%
Volume Distribution (VD):	0.593
Pgp-substrate:	6.751589298248291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.826
CYP1A2-substrate:	0.818
CYP2C19-inhibitor:	0.51
CYP2C19-substrate:	0.173
CYP2C9-inhibitor:	0.597
CYP2C9-substrate:	0.865
CYP2D6-inhibitor:	0.359
CYP2D6-substrate:	0.699
CYP3A4-inhibitor:	0.673
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	9.632
Half-life (T1/2):	0.255

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.773
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.822
Skin Sensitization:	0.039
Carcinogencity:	0.873
Eye Corrosion:	0.003
Eye Irritation:	0.255
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC77878

Natural Product ID:	NPC77878
*Common Name:**	Isofiliformine
IUPAC Name:	n.a.
Synonyms:	isofiliformine
Standard InCHIKey:	WQASXWBMZSTCJF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H13NO6/c1-23-12-6-9-10(5-11(12)21)16(22)15-13-8(3-4-20-15)17(24-2)19-18(14(9)13)25-7-26-19/h3-6,21H,7H2,1-2H3
SMILES:	COc1cc2c(cc1O)C(=O)c1c3c2c2OCOc2c(c3ccn1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403551
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18217715]
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3079	Cassytha filiformis	Species	Lauraceae	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
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	32000.0	nM	PMID[486837]

☑ 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 NPC77878 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	514
0.1-0.2	2493
0.2-0.3	9728
0.3-0.4	7632
0.4-0.5	7299
0.5-0.6	11942
0.6-0.7	2769
0.7-0.8	268
0.8-0.85	32
0.85-0.9	4
0.9-0.95	10
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.982	High Similarity	NPC183537
0.9682	High Similarity	NPC207283
0.9682	High Similarity	NPC84164
0.9638	High Similarity	NPC15406
0.9595	High Similarity	NPC124313
0.9548	High Similarity	NPC210296
0.9412	High Similarity	NPC189903
0.9412	High Similarity	NPC182907
0.9367	High Similarity	NPC108342
0.9321	High Similarity	NPC90875
0.9276	High Similarity	NPC22481
0.9231	High Similarity	NPC233334
0.9196	High Similarity	NPC166722
0.914	High Similarity	NPC278525
0.9054	High Similarity	NPC24019
0.8869	High Similarity	NPC210434
0.8616	High Similarity	NPC122463
0.8468	Intermediate Similarity	NPC146976
0.8462	Intermediate Similarity	NPC119134
0.8423	Intermediate Similarity	NPC236668
0.8306	Intermediate Similarity	NPC478045
0.8216	Intermediate Similarity	NPC134637
0.8214	Intermediate Similarity	NPC251160
0.821	Intermediate Similarity	NPC118121
0.8194	Intermediate Similarity	NPC204446
0.817	Intermediate Similarity	NPC253675
0.8125	Intermediate Similarity	NPC470020
0.8122	Intermediate Similarity	NPC174049
0.8114	Intermediate Similarity	NPC473822
0.8091	Intermediate Similarity	NPC107123
0.8057	Intermediate Similarity	NPC129897
0.8025	Intermediate Similarity	NPC270515
0.8	Intermediate Similarity	NPC132385
0.7965	Intermediate Similarity	NPC54066
0.7959	Intermediate Similarity	NPC302807
0.7957	Intermediate Similarity	NPC246381
0.7904	Intermediate Similarity	NPC235076
0.7899	Intermediate Similarity	NPC255800
0.7899	Intermediate Similarity	NPC96584
0.789	Intermediate Similarity	NPC201508
0.7885	Intermediate Similarity	NPC188420
0.7863	Intermediate Similarity	NPC322482
0.7803	Intermediate Similarity	NPC477019
0.7802	Intermediate Similarity	NPC100079
0.7802	Intermediate Similarity	NPC23614
0.7783	Intermediate Similarity	NPC149471
0.7783	Intermediate Similarity	NPC271215
0.7768	Intermediate Similarity	NPC46451
0.7739	Intermediate Similarity	NPC53069
0.7739	Intermediate Similarity	NPC202605
0.7739	Intermediate Similarity	NPC202768
0.7739	Intermediate Similarity	NPC112206
0.7739	Intermediate Similarity	NPC296482
0.7723	Intermediate Similarity	NPC234197
0.7722	Intermediate Similarity	NPC470018
0.7705	Intermediate Similarity	NPC217554
0.7689	Intermediate Similarity	NPC318068
0.7689	Intermediate Similarity	NPC74575
0.7683	Intermediate Similarity	NPC284141
0.7683	Intermediate Similarity	NPC208522
0.7675	Intermediate Similarity	NPC313189
0.7668	Intermediate Similarity	NPC224928
0.7664	Intermediate Similarity	NPC41501
0.7662	Intermediate Similarity	NPC171409
0.7662	Intermediate Similarity	NPC96405
0.7637	Intermediate Similarity	NPC94842
0.7623	Intermediate Similarity	NPC11408
0.7619	Intermediate Similarity	NPC220337
0.7598	Intermediate Similarity	NPC135549
0.7598	Intermediate Similarity	NPC193238
0.7585	Intermediate Similarity	NPC469439
0.7569	Intermediate Similarity	NPC282346
0.7568	Intermediate Similarity	NPC133140
0.7568	Intermediate Similarity	NPC195268
0.7562	Intermediate Similarity	NPC49547
0.7554	Intermediate Similarity	NPC474594
0.7542	Intermediate Similarity	NPC148409
0.7541	Intermediate Similarity	NPC470017
0.753	Intermediate Similarity	NPC137353
0.7529	Intermediate Similarity	NPC191489
0.7521	Intermediate Similarity	NPC55470
0.7521	Intermediate Similarity	NPC216612
0.7511	Intermediate Similarity	NPC210256
0.751	Intermediate Similarity	NPC476997
0.751	Intermediate Similarity	NPC470022
0.75	Intermediate Similarity	NPC473639
0.75	Intermediate Similarity	NPC215837
0.7479	Intermediate Similarity	NPC476998
0.7479	Intermediate Similarity	NPC476996
0.7479	Intermediate Similarity	NPC232225
0.7439	Intermediate Similarity	NPC476995
0.7438	Intermediate Similarity	NPC476994
0.7435	Intermediate Similarity	NPC476581
0.7435	Intermediate Similarity	NPC36229
0.7435	Intermediate Similarity	NPC16452
0.7419	Intermediate Similarity	NPC49672
0.7413	Intermediate Similarity	NPC88923
0.7413	Intermediate Similarity	NPC100734
0.7413	Intermediate Similarity	NPC315634
0.7412	Intermediate Similarity	NPC13603
0.741	Intermediate Similarity	NPC1608
0.7407	Intermediate Similarity	NPC469792
0.7393	Intermediate Similarity	NPC473833
0.7393	Intermediate Similarity	NPC89549
0.7382	Intermediate Similarity	NPC46990
0.7379	Intermediate Similarity	NPC253482
0.7373	Intermediate Similarity	NPC326930
0.7373	Intermediate Similarity	NPC53255
0.7373	Intermediate Similarity	NPC298449
0.7373	Intermediate Similarity	NPC85879
0.7373	Intermediate Similarity	NPC475301
0.7371	Intermediate Similarity	NPC474595
0.7368	Intermediate Similarity	NPC476578
0.7368	Intermediate Similarity	NPC4071
0.7368	Intermediate Similarity	NPC476582
0.7366	Intermediate Similarity	NPC101312
0.736	Intermediate Similarity	NPC475648
0.7359	Intermediate Similarity	NPC164374
0.7359	Intermediate Similarity	NPC137929
0.7355	Intermediate Similarity	NPC473506
0.7345	Intermediate Similarity	NPC146724
0.7344	Intermediate Similarity	NPC472589
0.7339	Intermediate Similarity	NPC207873
0.7339	Intermediate Similarity	NPC100573
0.7336	Intermediate Similarity	NPC328928
0.7325	Intermediate Similarity	NPC328186
0.7325	Intermediate Similarity	NPC477787
0.7325	Intermediate Similarity	NPC475631
0.7325	Intermediate Similarity	NPC475600
0.7325	Intermediate Similarity	NPC87152
0.7325	Intermediate Similarity	NPC122968
0.7325	Intermediate Similarity	NPC228377
0.7325	Intermediate Similarity	NPC476110
0.7311	Intermediate Similarity	NPC246658
0.7306	Intermediate Similarity	NPC475303
0.7306	Intermediate Similarity	NPC292416
0.7306	Intermediate Similarity	NPC473689
0.7306	Intermediate Similarity	NPC475596
0.7306	Intermediate Similarity	NPC316841
0.7304	Intermediate Similarity	NPC31930
0.7295	Intermediate Similarity	NPC471977
0.7295	Intermediate Similarity	NPC470486
0.7295	Intermediate Similarity	NPC471190
0.7295	Intermediate Similarity	NPC475644
0.7287	Intermediate Similarity	NPC475406
0.7277	Intermediate Similarity	NPC124086
0.7277	Intermediate Similarity	NPC474009
0.7276	Intermediate Similarity	NPC9482
0.7276	Intermediate Similarity	NPC320324
0.7276	Intermediate Similarity	NPC244839
0.7276	Intermediate Similarity	NPC319880
0.7276	Intermediate Similarity	NPC30456
0.7276	Intermediate Similarity	NPC471004
0.7269	Intermediate Similarity	NPC209981
0.7269	Intermediate Similarity	NPC471978
0.7266	Intermediate Similarity	NPC472588
0.7265	Intermediate Similarity	NPC90185
0.7258	Intermediate Similarity	NPC38959
0.7258	Intermediate Similarity	NPC327904
0.7257	Intermediate Similarity	NPC280964
0.7257	Intermediate Similarity	NPC141915
0.7257	Intermediate Similarity	NPC114335
0.7257	Intermediate Similarity	NPC266931
0.7255	Intermediate Similarity	NPC67401
0.7252	Intermediate Similarity	NPC471979
0.7252	Intermediate Similarity	NPC470042
0.7251	Intermediate Similarity	NPC72905
0.7249	Intermediate Similarity	NPC127085
0.7247	Intermediate Similarity	NPC237702
0.7247	Intermediate Similarity	NPC172222
0.7246	Intermediate Similarity	NPC220241
0.7246	Intermediate Similarity	NPC295479
0.7222	Intermediate Similarity	NPC142385
0.7222	Intermediate Similarity	NPC308943
0.722	Intermediate Similarity	NPC284685
0.7218	Intermediate Similarity	NPC327769
0.7218	Intermediate Similarity	NPC35208
0.7213	Intermediate Similarity	NPC200888
0.7205	Intermediate Similarity	NPC324619
0.7205	Intermediate Similarity	NPC475315
0.7203	Intermediate Similarity	NPC290689
0.7202	Intermediate Similarity	NPC76565
0.7202	Intermediate Similarity	NPC250807
0.7202	Intermediate Similarity	NPC57797
0.7197	Intermediate Similarity	NPC240684
0.719	Intermediate Similarity	NPC121069
0.7184	Intermediate Similarity	NPC211920
0.7184	Intermediate Similarity	NPC146824
0.7184	Intermediate Similarity	NPC116701
0.7178	Intermediate Similarity	NPC301368
0.7178	Intermediate Similarity	NPC84815
0.7174	Intermediate Similarity	NPC17677
0.7174	Intermediate Similarity	NPC193906
0.7174	Intermediate Similarity	NPC23080
0.7172	Intermediate Similarity	NPC473850
0.7172	Intermediate Similarity	NPC328154
0.7172	Intermediate Similarity	NPC475498
0.7172	Intermediate Similarity	NPC473449
0.7172	Intermediate Similarity	NPC475137
0.7171	Intermediate Similarity	NPC168922

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 NPC77878 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	652
0.2-0.3	1014
0.3-0.4	1890
0.4-0.5	2593
0.5-0.6	2046
0.6-0.7	602
0.7-0.8	38
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7967	Intermediate Similarity	NPD1483	Discontinued
0.7773	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD3763	Approved
0.7739	Intermediate Similarity	NPD3816	Phase 1
0.7739	Intermediate Similarity	NPD3815	Phase 1
0.768	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD7885	Phase 2
0.7664	Intermediate Similarity	NPD7886	Phase 2
0.7638	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD8091	Phase 3
0.7568	Intermediate Similarity	NPD3924	Approved
0.7568	Intermediate Similarity	NPD3923	Approved
0.7568	Intermediate Similarity	NPD3921	Approved
0.7568	Intermediate Similarity	NPD3922	Approved
0.7529	Intermediate Similarity	NPD7708	Approved
0.752	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7069	Discontinued
0.7419	Intermediate Similarity	NPD7417	Discontinued
0.7413	Intermediate Similarity	NPD7803	Approved
0.7404	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5805	Approved
0.7336	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6494	Phase 2
0.7248	Intermediate Similarity	NPD7169	Suspended
0.7233	Intermediate Similarity	NPD5488	Discontinued
0.722	Intermediate Similarity	NPD7955	Approved
0.722	Intermediate Similarity	NPD7956	Approved
0.7211	Intermediate Similarity	NPD6790	Phase 1
0.7208	Intermediate Similarity	NPD7395	Discontinued
0.7177	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4989	Phase 2
0.7143	Intermediate Similarity	NPD5866	Approved
0.7137	Intermediate Similarity	NPD4885	Approved
0.7072	Intermediate Similarity	NPD3920	Phase 2
0.7061	Intermediate Similarity	NPD6531	Approved
0.7061	Intermediate Similarity	NPD6530	Approved
0.7057	Intermediate Similarity	NPD7673	Phase 3
0.7054	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6716	Phase 1
0.7029	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5482	Discontinued
0.7009	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6242	Discontinued
0.7	Intermediate Similarity	NPD6361	Phase 2
0.6979	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6723	Discontinued
0.6955	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3263	Phase 3
0.6933	Remote Similarity	NPD5429	Discontinued
0.6933	Remote Similarity	NPD3386	Phase 2
0.6926	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD6568	Discontinued
0.6914	Remote Similarity	NPD6517	Phase 3
0.6905	Remote Similarity	NPD4373	Phase 2
0.6899	Remote Similarity	NPD8468	Phase 2
0.6898	Remote Similarity	NPD2899	Discontinued
0.6886	Remote Similarity	NPD4375	Approved
0.688	Remote Similarity	NPD7654	Discontinued
0.6877	Remote Similarity	NPD6964	Approved
0.6877	Remote Similarity	NPD6963	Approved
0.687	Remote Similarity	NPD8479	Phase 2
0.6863	Remote Similarity	NPD6727	Phase 2
0.6857	Remote Similarity	NPD3354	Phase 2
0.6856	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5022	Discontinued
0.685	Remote Similarity	NPD3217	Phase 2
0.6844	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7558	Phase 2
0.6838	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD3925	Approved
0.6825	Remote Similarity	NPD1505	Phase 2
0.6825	Remote Similarity	NPD6962	Phase 2
0.6807	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7426	Phase 1
0.6792	Remote Similarity	NPD8461	Discontinued
0.6792	Remote Similarity	NPD7222	Phase 2
0.6789	Remote Similarity	NPD4429	Discontinued
0.6786	Remote Similarity	NPD4952	Phase 3
0.6778	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5612	Discontinued
0.6773	Remote Similarity	NPD3259	Approved
0.6773	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8016	Phase 3
0.6769	Remote Similarity	NPD4889	Approved
0.6769	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6974	Phase 3
0.675	Remote Similarity	NPD5530	Phase 1
0.6747	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6745	Discontinued
0.6733	Remote Similarity	NPD5640	Discontinued
0.6732	Remote Similarity	NPD6825	Phase 1
0.6719	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7924	Phase 2
0.6716	Remote Similarity	NPD7925	Phase 2
0.6708	Remote Similarity	NPD31	Approved
0.6708	Remote Similarity	NPD4037	Approved
0.6708	Remote Similarity	NPD4035	Approved
0.6708	Remote Similarity	NPD32	Approved
0.6708	Remote Similarity	NPD4036	Approved
0.6708	Remote Similarity	NPD4039	Approved
0.6708	Remote Similarity	NPD4038	Approved
0.6708	Remote Similarity	NPD4034	Approved
0.6708	Remote Similarity	NPD4122	Approved
0.6708	Remote Similarity	NPD4033	Approved
0.6707	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4923	Phase 1
0.6707	Remote Similarity	NPD8149	Discontinued
0.6706	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4845	Discontinued
0.6705	Remote Similarity	NPD7859	Phase 2
0.6704	Remote Similarity	NPD5450	Discontinued
0.6703	Remote Similarity	NPD7689	Approved
0.6695	Remote Similarity	NPD6975	Discontinued
0.6694	Remote Similarity	NPD5519	Discontinued
0.6693	Remote Similarity	NPD4846	Phase 2
0.6692	Remote Similarity	NPD7588	Discontinued
0.6681	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7555	Discontinued
0.6679	Remote Similarity	NPD5532	Phase 2
0.6679	Remote Similarity	NPD6228	Discontinued
0.6667	Remote Similarity	NPD6569	Phase 2
0.6667	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6655	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD7567	Approved
0.6654	Remote Similarity	NPD3006	Discontinued
0.6653	Remote Similarity	NPD7827	Phase 1
0.6641	Remote Similarity	NPD7922	Phase 1
0.6641	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5914	Approved
0.6638	Remote Similarity	NPD4551	Phase 2
0.6627	Remote Similarity	NPD3258	Approved
0.6626	Remote Similarity	NPD5658	Approved
0.6617	Remote Similarity	NPD8463	Approved
0.6616	Remote Similarity	NPD6276	Discontinued
0.6616	Remote Similarity	NPD3328	Phase 2
0.6615	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4502	Phase 2
0.6612	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4418	Discontinued
0.6606	Remote Similarity	NPD5459	Phase 2
0.6603	Remote Similarity	NPD6230	Discontinued
0.66	Remote Similarity	NPD7180	Phase 3
0.66	Remote Similarity	NPD5850	Phase 3
0.6598	Remote Similarity	NPD5513	Phase 2
0.6589	Remote Similarity	NPD7853	Phase 2
0.6587	Remote Similarity	NPD7279	Phase 2
0.6587	Remote Similarity	NPD7278	Phase 2
0.6587	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6586	Remote Similarity	NPD6198	Phase 1
0.6584	Remote Similarity	NPD7452	Approved
0.6584	Remote Similarity	NPD7453	Approved
0.6582	Remote Similarity	NPD5512	Phase 3
0.6581	Remote Similarity	NPD6281	Approved
0.6579	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4328	Approved
0.6574	Remote Similarity	NPD5507	Approved
0.6574	Remote Similarity	NPD6298	Discontinued
0.6574	Remote Similarity	NPD5506	Approved
0.657	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8101	Phase 3
0.6566	Remote Similarity	NPD3809	Discontinued
0.6564	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8067	Phase 3
0.656	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3795	Approved
0.6559	Remote Similarity	NPD3794	Approved
0.6557	Remote Similarity	NPD4859	Phase 1
0.6557	Remote Similarity	NPD6376	Discontinued
0.6556	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5005	Approved
0.6556	Remote Similarity	NPD5006	Approved
0.6555	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2951	Discontinued
0.6548	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD8356	Approved
0.6548	Remote Similarity	NPD1856	Discontinued
0.6543	Remote Similarity	NPD7010	Phase 3
0.6542	Remote Similarity	NPD6219	Discontinued
0.6538	Remote Similarity	NPD7234	Approved
0.6538	Remote Similarity	NPD7233	Approved
0.6533	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3257	Approved
0.6531	Remote Similarity	NPD8151	Discontinued
0.6528	Remote Similarity	NPD4558	Phase 2
0.6527	Remote Similarity	NPD4875	Phase 3
0.6527	Remote Similarity	NPD4876	Phase 3
0.6525	Remote Similarity	NPD5891	Approved
0.652	Remote Similarity	NPD5632	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