NPASS Compound

Structure

NPC18661 OpenBabel07101719252D 33 38 0 0 1 0 0 0 0 0999 V2000 5.8863 -1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4113 -1.0773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8227 -1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3864 -0.8679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0109 0.1814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0109 -0.7686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1881 0.6564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1881 -1.2436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 0.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 -1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1136 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 -1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2909 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9035 1.2436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3654 0.1814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4619 0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3654 -0.7686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1136 -1.4250 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4682 -1.4250 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9035 -0.2936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4682 1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9363 -1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 -0.4750 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 2.4682 -0.4750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4619 -1.0621 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2909 1.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 1.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9363 -2.8500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2909 -1.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 17 2 0 0 0 0 8 19 2 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 27 1 6 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 23 2 0 0 0 0 19 29 1 0 0 0 0 20 26 1 1 0 0 0 20 28 1 0 0 0 0 21 25 1 1 0 0 0 21 33 1 0 0 0 0 22 28 1 1 0 0 0 22 33 1 0 0 0 0 23 27 1 0 0 0 0 23 29 1 0 0 0 0 24 30 2 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 27 1 6 0 0 0 27 4 1 6 0 0 0 28 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	451.27
Volume:	474.481
LogP:	4.625
LogD:	3.6
LogS:	-3.694
# Rotatable Bonds:	2
TPSA:	82.55
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	4.711
Fsp3:	0.679
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.021
MDCK Permeability:	2.237054650322534e-05
Pgp-inhibitor:	0.9
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.703
Plasma Protein Binding (PPB):	91.10704040527344%
Volume Distribution (VD):	0.248
Pgp-substrate:	7.075159072875977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.75
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.17
CYP2C9-substrate:	0.19
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.269
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	2.224
Half-life (T1/2):	0.133

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.361
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.682
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.842
Carcinogencity:	0.559
Eye Corrosion:	0.026
Eye Irritation:	0.057
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC18661

Natural Product ID:	NPC18661
*Common Name:**	QHCUDWQJVPGPRW-JKEWKBHPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QHCUDWQJVPGPRW-JKEWKBHPSA-N
Standard InCHI:	InChI=1S/C28H37NO4/c1-25(2,32)21-12-14-28(24(30)31)20-10-9-16-15-18-17-7-5-6-8-19(17)29-23(18)27(16,4)26(20,3)13-11-22(28)33-21/h5-8,16,20-22,29,32H,9-15H2,1-4H3,(H,30,31)/t16-,20+,21-,22-,26-,27+,28+/m0/s1
SMILES:	CC(C)([C@@H]1CC[C@]2([C@@H]3CC[C@H]4Cc5c6ccccc6[nH]c5[C@]4(C)[C@@]3(C)CC[C@@H]2O1)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2408949
PubChem CID:	71745336
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003557] 19-oxosteroids

*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
NPO32542	penicillium camemberti oucmdz-1492	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23886345]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	38900.0	nM	PMID[529699]

☑ 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 NPC18661 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	287
0.1-0.2	1329
0.2-0.3	3379
0.3-0.4	12978
0.4-0.5	19377
0.5-0.6	3751
0.6-0.7	1322
0.7-0.8	217
0.8-0.85	41
0.85-0.9	15
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8956	High Similarity	NPC165201
0.8913	High Similarity	NPC119700
0.8883	High Similarity	NPC231342
0.8859	High Similarity	NPC99428
0.8782	High Similarity	NPC235900
0.8693	High Similarity	NPC471284
0.8634	High Similarity	NPC79107
0.8634	High Similarity	NPC475424
0.8608	High Similarity	NPC123019
0.8607	High Similarity	NPC96131
0.8564	High Similarity	NPC34271
0.8541	High Similarity	NPC302191
0.8519	High Similarity	NPC206967
0.8438	Intermediate Similarity	NPC181502
0.8438	Intermediate Similarity	NPC85066
0.8415	Intermediate Similarity	NPC97525
0.839	Intermediate Similarity	NPC61813
0.8387	Intermediate Similarity	NPC198339
0.8218	Intermediate Similarity	NPC475165
0.8177	Intermediate Similarity	NPC250129
0.816	Intermediate Similarity	NPC473806
0.816	Intermediate Similarity	NPC471634
0.8138	Intermediate Similarity	NPC6093
0.8131	Intermediate Similarity	NPC475151
0.8122	Intermediate Similarity	NPC473747
0.8079	Intermediate Similarity	NPC284102
0.804	Intermediate Similarity	NPC81654
0.804	Intermediate Similarity	NPC313985
0.804	Intermediate Similarity	NPC49196
0.804	Intermediate Similarity	NPC195461
0.804	Intermediate Similarity	NPC249150
0.804	Intermediate Similarity	NPC79129
0.8037	Intermediate Similarity	NPC282033
0.801	Intermediate Similarity	NPC473547
0.7971	Intermediate Similarity	NPC97388
0.794	Intermediate Similarity	NPC50503
0.7931	Intermediate Similarity	NPC187456
0.7892	Intermediate Similarity	NPC474905
0.7874	Intermediate Similarity	NPC475778
0.7864	Intermediate Similarity	NPC234999
0.7833	Intermediate Similarity	NPC476115
0.7826	Intermediate Similarity	NPC204303
0.7799	Intermediate Similarity	NPC473650
0.7799	Intermediate Similarity	NPC160527
0.7778	Intermediate Similarity	NPC126492
0.7766	Intermediate Similarity	NPC154293
0.7757	Intermediate Similarity	NPC266192
0.7713	Intermediate Similarity	NPC94541
0.7713	Intermediate Similarity	NPC470843
0.7706	Intermediate Similarity	NPC290529
0.7685	Intermediate Similarity	NPC267926
0.7668	Intermediate Similarity	NPC213468
0.765	Intermediate Similarity	NPC57690
0.7642	Intermediate Similarity	NPC249428
0.7639	Intermediate Similarity	NPC141428
0.7629	Intermediate Similarity	NPC300688
0.7586	Intermediate Similarity	NPC52557
0.757	Intermediate Similarity	NPC475476
0.757	Intermediate Similarity	NPC242446
0.7538	Intermediate Similarity	NPC175474
0.7524	Intermediate Similarity	NPC474116
0.7524	Intermediate Similarity	NPC162730
0.7523	Intermediate Similarity	NPC82070
0.7512	Intermediate Similarity	NPC476114
0.7512	Intermediate Similarity	NPC204491
0.7512	Intermediate Similarity	NPC470280
0.7488	Intermediate Similarity	NPC205403
0.7488	Intermediate Similarity	NPC477135
0.7488	Intermediate Similarity	NPC52254
0.7477	Intermediate Similarity	NPC235885
0.7431	Intermediate Similarity	NPC475271
0.7429	Intermediate Similarity	NPC127677
0.7427	Intermediate Similarity	NPC214428
0.7426	Intermediate Similarity	NPC55493
0.7422	Intermediate Similarity	NPC473565
0.7383	Intermediate Similarity	NPC313640
0.7381	Intermediate Similarity	NPC46225
0.7379	Intermediate Similarity	NPC241024
0.7373	Intermediate Similarity	NPC470874
0.7364	Intermediate Similarity	NPC472762
0.7363	Intermediate Similarity	NPC46413
0.7356	Intermediate Similarity	NPC476874
0.7352	Intermediate Similarity	NPC147446
0.7349	Intermediate Similarity	NPC203614
0.7347	Intermediate Similarity	NPC151939
0.7343	Intermediate Similarity	NPC312870
0.7343	Intermediate Similarity	NPC199851
0.7343	Intermediate Similarity	NPC254240
0.7343	Intermediate Similarity	NPC128265
0.7343	Intermediate Similarity	NPC294909
0.7333	Intermediate Similarity	NPC277350
0.733	Intermediate Similarity	NPC477044
0.733	Intermediate Similarity	NPC477041
0.7327	Intermediate Similarity	NPC329858
0.7317	Intermediate Similarity	NPC11445
0.7295	Intermediate Similarity	NPC32200
0.7295	Intermediate Similarity	NPC477045
0.729	Intermediate Similarity	NPC151976
0.7286	Intermediate Similarity	NPC139291
0.7286	Intermediate Similarity	NPC472108
0.7268	Intermediate Similarity	NPC157828
0.7268	Intermediate Similarity	NPC195239
0.7264	Intermediate Similarity	NPC258062
0.726	Intermediate Similarity	NPC2395
0.7252	Intermediate Similarity	NPC249342
0.7246	Intermediate Similarity	NPC102008
0.7241	Intermediate Similarity	NPC314333
0.7238	Intermediate Similarity	NPC98715
0.723	Intermediate Similarity	NPC469743
0.7222	Intermediate Similarity	NPC270009
0.7217	Intermediate Similarity	NPC225821
0.7216	Intermediate Similarity	NPC201700
0.7214	Intermediate Similarity	NPC476319
0.7204	Intermediate Similarity	NPC477043
0.7202	Intermediate Similarity	NPC281049
0.7202	Intermediate Similarity	NPC174788
0.72	Intermediate Similarity	NPC472444
0.72	Intermediate Similarity	NPC19679
0.719	Intermediate Similarity	NPC193761
0.7178	Intermediate Similarity	NPC235684
0.7176	Intermediate Similarity	NPC229348
0.7175	Intermediate Similarity	NPC470873
0.7171	Intermediate Similarity	NPC67551
0.7168	Intermediate Similarity	NPC70155
0.7162	Intermediate Similarity	NPC245756
0.7157	Intermediate Similarity	NPC472586
0.715	Intermediate Similarity	NPC477548
0.715	Intermediate Similarity	NPC271862
0.715	Intermediate Similarity	NPC71037
0.715	Intermediate Similarity	NPC478158
0.7143	Intermediate Similarity	NPC478157
0.7143	Intermediate Similarity	NPC33949
0.7143	Intermediate Similarity	NPC300183
0.7137	Intermediate Similarity	NPC476516
0.713	Intermediate Similarity	NPC87856
0.713	Intermediate Similarity	NPC112547
0.7124	Intermediate Similarity	NPC474192
0.7124	Intermediate Similarity	NPC475720
0.711	Intermediate Similarity	NPC30570
0.711	Intermediate Similarity	NPC132211
0.7105	Intermediate Similarity	NPC471458
0.7098	Intermediate Similarity	NPC328186
0.7098	Intermediate Similarity	NPC475631
0.7098	Intermediate Similarity	NPC476110
0.7098	Intermediate Similarity	NPC475600
0.7098	Intermediate Similarity	NPC122968
0.7098	Intermediate Similarity	NPC211920
0.7098	Intermediate Similarity	NPC87152
0.7098	Intermediate Similarity	NPC228377
0.7098	Intermediate Similarity	NPC477787
0.7097	Intermediate Similarity	NPC267965
0.7097	Intermediate Similarity	NPC472291
0.7094	Intermediate Similarity	NPC315555
0.7087	Intermediate Similarity	NPC472113
0.7087	Intermediate Similarity	NPC253482
0.7073	Intermediate Similarity	NPC472112
0.7072	Intermediate Similarity	NPC41318
0.7072	Intermediate Similarity	NPC469312
0.7067	Intermediate Similarity	NPC470486
0.7067	Intermediate Similarity	NPC471190
0.7067	Intermediate Similarity	NPC471977
0.7067	Intermediate Similarity	NPC475644
0.7062	Intermediate Similarity	NPC40779
0.7056	Intermediate Similarity	NPC6982
0.7056	Intermediate Similarity	NPC477065
0.7053	Intermediate Similarity	NPC200743
0.705	Intermediate Similarity	NPC219336
0.705	Intermediate Similarity	NPC472443
0.7047	Intermediate Similarity	NPC473320
0.7046	Intermediate Similarity	NPC131273
0.7046	Intermediate Similarity	NPC473441
0.7041	Intermediate Similarity	NPC78020
0.7039	Intermediate Similarity	NPC472097
0.7031	Intermediate Similarity	NPC57453
0.703	Intermediate Similarity	NPC469358
0.703	Intermediate Similarity	NPC472110
0.703	Intermediate Similarity	NPC472109
0.7028	Intermediate Similarity	NPC137589
0.7024	Intermediate Similarity	NPC63199
0.7024	Intermediate Similarity	NPC196251
0.7024	Intermediate Similarity	NPC111602
0.7024	Intermediate Similarity	NPC102338
0.7023	Intermediate Similarity	NPC61637
0.7022	Intermediate Similarity	NPC124029
0.702	Intermediate Similarity	NPC34508
0.7018	Intermediate Similarity	NPC473105
0.7015	Intermediate Similarity	NPC469896
0.7014	Intermediate Similarity	NPC84815
0.7014	Intermediate Similarity	NPC301368
0.7009	Intermediate Similarity	NPC328154
0.7005	Intermediate Similarity	NPC47190
0.7004	Intermediate Similarity	NPC316841
0.7004	Intermediate Similarity	NPC292416
0.7004	Intermediate Similarity	NPC473689
0.7004	Intermediate Similarity	NPC96801
0.7004	Intermediate Similarity	NPC475303
0.7004	Intermediate Similarity	NPC475596
0.7004	Intermediate Similarity	NPC150698
0.7	Intermediate Similarity	NPC149708
0.7	Intermediate Similarity	NPC217372

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 NPC18661 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	518
0.2-0.3	643
0.3-0.4	2021
0.4-0.5	3688
0.5-0.6	1720
0.6-0.7	333
0.7-0.8	25
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
0.804	Intermediate Similarity	NPD4600	Approved
0.804	Intermediate Similarity	NPD4601	Approved
0.7727	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5003	Discontinued
0.7547	Intermediate Similarity	NPD7707	Approved
0.7461	Intermediate Similarity	NPD43	Approved
0.7461	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD6182	Approved
0.7413	Intermediate Similarity	NPD2565	Phase 2
0.7413	Intermediate Similarity	NPD2564	Approved
0.7409	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5899	Approved
0.736	Intermediate Similarity	NPD5897	Approved
0.736	Intermediate Similarity	NPD5898	Approved
0.7343	Intermediate Similarity	NPD4501	Approved
0.7343	Intermediate Similarity	NPD4500	Approved
0.7333	Intermediate Similarity	NPD7957	Phase 1
0.7333	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7778	Approved
0.7246	Intermediate Similarity	NPD53	Approved
0.7246	Intermediate Similarity	NPD7777	Approved
0.7241	Intermediate Similarity	NPD4499	Approved
0.7192	Intermediate Similarity	NPD7233	Approved
0.7192	Intermediate Similarity	NPD7234	Approved
0.7156	Intermediate Similarity	NPD2920	Discontinued
0.7114	Intermediate Similarity	NPD2095	Phase 2
0.7114	Intermediate Similarity	NPD2092	Phase 2
0.7114	Intermediate Similarity	NPD2094	Phase 2
0.7103	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2091	Phase 2
0.7079	Intermediate Similarity	NPD2096	Phase 2
0.7048	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2844	Phase 3
0.7026	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8325	Phase 3
0.7	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8326	Phase 3
0.6971	Remote Similarity	NPD7708	Approved
0.6967	Remote Similarity	NPD6249	Phase 2
0.6967	Remote Similarity	NPD6248	Phase 2
0.695	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD4602	Approved
0.6927	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6176	Phase 1
0.6915	Remote Similarity	NPD6642	Approved
0.6915	Remote Similarity	NPD6641	Approved
0.6912	Remote Similarity	NPD4506	Discontinued
0.69	Remote Similarity	NPD482	Approved
0.6892	Remote Similarity	NPD7878	Phase 2
0.6888	Remote Similarity	NPD6635	Approved
0.6881	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5501	Discontinued
0.686	Remote Similarity	NPD7955	Approved
0.686	Remote Similarity	NPD1534	Approved
0.686	Remote Similarity	NPD7956	Approved
0.6857	Remote Similarity	NPD7803	Approved
0.6849	Remote Similarity	NPD7470	Discontinued
0.682	Remote Similarity	NPD5429	Discontinued
0.6812	Remote Similarity	NPD8431	Approved
0.6808	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8399	Phase 1
0.6789	Remote Similarity	NPD8423	Phase 2
0.678	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4334	Discontinued
0.6776	Remote Similarity	NPD6479	Discontinued
0.6774	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5487	Phase 1
0.6759	Remote Similarity	NPD8072	Approved
0.6758	Remote Similarity	NPD7941	Phase 3
0.6753	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8466	Approved
0.6746	Remote Similarity	NPD8467	Approved
0.6746	Remote Similarity	NPD8465	Approved
0.6745	Remote Similarity	NPD5512	Phase 3
0.6742	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD5913	Phase 3
0.6714	Remote Similarity	NPD6206	Phase 1
0.6713	Remote Similarity	NPD8073	Approved
0.6712	Remote Similarity	NPD7277	Approved
0.6712	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7276	Approved
0.6698	Remote Similarity	NPD7944	Discontinued
0.6697	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD750	Phase 2
0.6683	Remote Similarity	NPD5473	Discontinued
0.6682	Remote Similarity	NPD6261	Phase 3
0.668	Remote Similarity	NPD8428	Approved
0.668	Remote Similarity	NPD8427	Approved
0.668	Remote Similarity	NPD8429	Approved
0.6667	Remote Similarity	NPD7865	Approved
0.6667	Remote Similarity	NPD7824	Approved
0.6667	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6178	Phase 3
0.6652	Remote Similarity	NPD7953	Approved
0.6652	Remote Similarity	NPD7952	Approved
0.6652	Remote Similarity	NPD7791	Approved
0.6652	Remote Similarity	NPD7789	Approved
0.6652	Remote Similarity	NPD7790	Approved
0.6652	Remote Similarity	NPD7950	Approved
0.6652	Remote Similarity	NPD7951	Approved
0.6651	Remote Similarity	NPD8115	Approved
0.6651	Remote Similarity	NPD8114	Approved
0.6641	Remote Similarity	NPD8460	Approved
0.6641	Remote Similarity	NPD8425	Approved
0.6641	Remote Similarity	NPD8426	Approved
0.6641	Remote Similarity	NPD8459	Approved
0.664	Remote Similarity	NPD8364	Approved
0.664	Remote Similarity	NPD8363	Approved
0.6637	Remote Similarity	NPD3795	Approved
0.6637	Remote Similarity	NPD3794	Approved
0.6636	Remote Similarity	NPD2510	Approved
0.6636	Remote Similarity	NPD2509	Approved
0.6636	Remote Similarity	NPD7187	Phase 2
0.6623	Remote Similarity	NPD6995	Phase 1
0.6622	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.662	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4897	Phase 2
0.6606	Remote Similarity	NPD5835	Phase 3
0.6606	Remote Similarity	NPD5834	Phase 3
0.6604	Remote Similarity	NPD4315	Phase 2
0.6603	Remote Similarity	NPD5444	Phase 1
0.6601	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4463	Approved
0.6598	Remote Similarity	NPD4462	Approved
0.6597	Remote Similarity	NPD8412	Phase 1
0.6592	Remote Similarity	NPD7455	Approved
0.6592	Remote Similarity	NPD7069	Discontinued
0.6592	Remote Similarity	NPD7454	Approved
0.659	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD6550	Discontinued
0.6587	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2144	Approved
0.6584	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD8468	Phase 2
0.658	Remote Similarity	NPD7731	Approved
0.658	Remote Similarity	NPD7730	Approved
0.6579	Remote Similarity	NPD5507	Approved
0.6579	Remote Similarity	NPD5506	Approved
0.6578	Remote Similarity	NPD3389	Approved
0.6578	Remote Similarity	NPD3393	Approved
0.6578	Remote Similarity	NPD3394	Approved
0.6575	Remote Similarity	NPD8282	Approved
0.6575	Remote Similarity	NPD5426	Phase 3
0.6575	Remote Similarity	NPD5901	Discontinued
0.6575	Remote Similarity	NPD56	Approved
0.6575	Remote Similarity	NPD8283	Approved
0.6574	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3038	Discontinued
0.6567	Remote Similarity	NPD7688	Phase 1
0.6565	Remote Similarity	NPD7271	Approved
0.6564	Remote Similarity	NPD6770	Approved
0.6562	Remote Similarity	NPD8094	Discontinued
0.6561	Remote Similarity	NPD2916	Discontinued
0.6558	Remote Similarity	NPD6664	Approved
0.6557	Remote Similarity	NPD4918	Discontinued
0.6553	Remote Similarity	NPD4079	Approved
0.6553	Remote Similarity	NPD8386	Phase 2
0.6553	Remote Similarity	NPD4076	Approved
0.655	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6026	Approved
0.6542	Remote Similarity	NPD7619	Phase 3
0.6542	Remote Similarity	NPD7618	Phase 3
0.6538	Remote Similarity	NPD5596	Phase 2
0.6538	Remote Similarity	NPD7962	Phase 2
0.6537	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5021	Discontinued
0.6532	Remote Similarity	NPD4520	Approved
0.6528	Remote Similarity	NPD7946	Pre-registration
0.6524	Remote Similarity	NPD8374	Phase 3
0.6522	Remote Similarity	NPD6595	Phase 3
0.6518	Remote Similarity	NPD8093	Discontinued
0.6516	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD8322	Phase 2
0.6516	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7727	Phase 2
0.6507	Remote Similarity	NPD7483	Phase 2
0.6507	Remote Similarity	NPD7482	Phase 2
0.6505	Remote Similarity	NPD3506	Approved
0.6505	Remote Similarity	NPD3505	Approved
0.6504	Remote Similarity	NPD7496	Phase 2
0.6504	Remote Similarity	NPD8160	Phase 2
0.6502	Remote Similarity	NPD1326	Approved
0.6502	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7474	Suspended
0.6502	Remote Similarity	NPD1325	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