NPASS Compound

Structure

NPC470177 OpenBabel07101718222D 24 26 0 0 1 0 0 0 0 0999 V2000 5.9154 -3.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7814 -2.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6968 -2.2905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2042 -2.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7096 -1.7403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 -2.7760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5605 -2.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1833 -2.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 -0.5290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9154 -2.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3173 -2.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0493 -2.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3173 -1.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1266 -1.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0493 -1.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1833 -0.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9972 0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5605 -0.7515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9154 -0.6525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1833 0.3475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 0.9757 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 12 2 0 0 0 0 7 15 2 0 0 0 0 8 12 1 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 9 20 1 0 0 0 0 10 19 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 16 1 0 0 0 0 14 17 2 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.17
Volume:	348.149
LogP:	3.817
LogD:	2.815
LogS:	-3.607
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.435
Synthetic Accessibility Score:	4.44
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.8
MDCK Permeability:	1.8070906662615016e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.263
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.926
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	95.74117279052734%
Volume Distribution (VD):	2.082
Pgp-substrate:	4.558470726013184%

ADMET: Metabolism

CYP1A2-inhibitor:	0.901
CYP1A2-substrate:	0.55
CYP2C19-inhibitor:	0.239
CYP2C19-substrate:	0.555
CYP2C9-inhibitor:	0.374
CYP2C9-substrate:	0.8
CYP2D6-inhibitor:	0.292
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.713
CYP3A4-substrate:	0.698

ADMET: Excretion

Clearance (CL):	4.941
Half-life (T1/2):	0.632

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.218
Drug-inuced Liver Injury (DILI):	0.535
AMES Toxicity:	0.184
Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.166
Skin Sensitization:	0.11
Carcinogencity:	0.886
Eye Corrosion:	0.044
Eye Irritation:	0.873
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC470177

Natural Product ID:	NPC470177
*Common Name:**	Neobharangin
IUPAC Name:	(11aS)-10-hydroxy-4,4,11a-trimethyl-8-propan-2-yl-3,11-dihydrobenzo[3,4]cyclohepta[3,5-c]pyran-1,9-dione
Synonyms:	Neobharangin
Standard InCHIKey:	RZVOPZIGXRIWOR-FQEVSTJZSA-N
Standard InCHI:	InChI=1S/C20H24O4/c1-11(2)13-8-12-6-7-15-19(3,4)10-24-18(23)20(15,5)9-14(12)17(22)16(13)21/h6-8,11,22H,9-10H2,1-5H3/t20-/m0/s1
SMILES:	CC(C)C1=CC2=CC=C3C(COC(=O)C3(CC2=C(C1=O)O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1807754
PubChem CID:	56673601
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
NPO33238	pygmacopremna herbacea	Species	n.a.	n.a.	roots	n.a.	n.a.	PMID[21708464]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.39	ug.mL-1	PMID[505139]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2.61	ug.mL-1	PMID[505139]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	13.0	ug.mL-1	PMID[505139]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	48.6	ug.mL-1	PMID[505139]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	104.4	ug.mL-1	PMID[505139]

☑ 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 NPC470177 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	171
0.1-0.2	965
0.2-0.3	4588
0.3-0.4	11451
0.4-0.5	13371
0.5-0.6	7581
0.6-0.7	4120
0.7-0.8	443
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8851	High Similarity	NPC45579
0.7957	Intermediate Similarity	NPC295347
0.7955	Intermediate Similarity	NPC32037
0.7955	Intermediate Similarity	NPC474680
0.7789	Intermediate Similarity	NPC208094
0.7753	Intermediate Similarity	NPC90287
0.7742	Intermediate Similarity	NPC263780
0.7738	Intermediate Similarity	NPC110725
0.7727	Intermediate Similarity	NPC105803
0.7711	Intermediate Similarity	NPC147438
0.7667	Intermediate Similarity	NPC234038
0.7634	Intermediate Similarity	NPC470036
0.7634	Intermediate Similarity	NPC174167
0.7614	Intermediate Similarity	NPC103486
0.7609	Intermediate Similarity	NPC210216
0.7604	Intermediate Similarity	NPC202705
0.7576	Intermediate Similarity	NPC179208
0.7558	Intermediate Similarity	NPC74410
0.7556	Intermediate Similarity	NPC241512
0.7556	Intermediate Similarity	NPC8518
0.7556	Intermediate Similarity	NPC263997
0.7556	Intermediate Similarity	NPC132228
0.7556	Intermediate Similarity	NPC6185
0.7553	Intermediate Similarity	NPC109414
0.7551	Intermediate Similarity	NPC469851
0.7529	Intermediate Similarity	NPC180886
0.7529	Intermediate Similarity	NPC26504
0.7528	Intermediate Similarity	NPC102197
0.75	Intermediate Similarity	NPC225515
0.75	Intermediate Similarity	NPC55869
0.75	Intermediate Similarity	NPC90055
0.7473	Intermediate Similarity	NPC203795
0.7471	Intermediate Similarity	NPC27817
0.747	Intermediate Similarity	NPC288667
0.7449	Intermediate Similarity	NPC472972
0.7447	Intermediate Similarity	NPC472705
0.7447	Intermediate Similarity	NPC36491
0.7447	Intermediate Similarity	NPC219874
0.7444	Intermediate Similarity	NPC196487
0.7444	Intermediate Similarity	NPC14575
0.7442	Intermediate Similarity	NPC283087
0.7439	Intermediate Similarity	NPC474060
0.7439	Intermediate Similarity	NPC94488
0.7423	Intermediate Similarity	NPC170131
0.7419	Intermediate Similarity	NPC5509
0.7419	Intermediate Similarity	NPC36668
0.7419	Intermediate Similarity	NPC212598
0.7419	Intermediate Similarity	NPC284561
0.7419	Intermediate Similarity	NPC112454
0.7419	Intermediate Similarity	NPC118011
0.7416	Intermediate Similarity	NPC471326
0.7416	Intermediate Similarity	NPC221231
0.7396	Intermediate Similarity	NPC777
0.7396	Intermediate Similarity	NPC300710
0.7396	Intermediate Similarity	NPC209355
0.7391	Intermediate Similarity	NPC476079
0.7391	Intermediate Similarity	NPC103743
0.7391	Intermediate Similarity	NPC113370
0.7391	Intermediate Similarity	NPC473097
0.7386	Intermediate Similarity	NPC108955
0.7386	Intermediate Similarity	NPC74086
0.7386	Intermediate Similarity	NPC304795
0.7368	Intermediate Similarity	NPC476416
0.7363	Intermediate Similarity	NPC307112
0.7356	Intermediate Similarity	NPC189485
0.7356	Intermediate Similarity	NPC471220
0.7347	Intermediate Similarity	NPC222011
0.734	Intermediate Similarity	NPC265856
0.7333	Intermediate Similarity	NPC16488
0.7333	Intermediate Similarity	NPC258985
0.7326	Intermediate Similarity	NPC470525
0.7326	Intermediate Similarity	NPC472967
0.7326	Intermediate Similarity	NPC40353
0.7326	Intermediate Similarity	NPC266159
0.732	Intermediate Similarity	NPC255410
0.7317	Intermediate Similarity	NPC134385
0.7312	Intermediate Similarity	NPC472008
0.7312	Intermediate Similarity	NPC60765
0.7303	Intermediate Similarity	NPC275766
0.7303	Intermediate Similarity	NPC327002
0.7303	Intermediate Similarity	NPC278459
0.7303	Intermediate Similarity	NPC121984
0.73	Intermediate Similarity	NPC473596
0.7294	Intermediate Similarity	NPC160540
0.7294	Intermediate Similarity	NPC213223
0.7292	Intermediate Similarity	NPC476415
0.7283	Intermediate Similarity	NPC202394
0.7283	Intermediate Similarity	NPC261721
0.7283	Intermediate Similarity	NPC198314
0.7283	Intermediate Similarity	NPC220478
0.7283	Intermediate Similarity	NPC472009
0.7283	Intermediate Similarity	NPC229717
0.7273	Intermediate Similarity	NPC327674
0.7273	Intermediate Similarity	NPC63649
0.7273	Intermediate Similarity	NPC264227
0.7273	Intermediate Similarity	NPC472965
0.7273	Intermediate Similarity	NPC192329
0.7273	Intermediate Similarity	NPC158565
0.7273	Intermediate Similarity	NPC475681
0.7263	Intermediate Similarity	NPC166110
0.7262	Intermediate Similarity	NPC474539
0.7255	Intermediate Similarity	NPC469852
0.7253	Intermediate Similarity	NPC474359
0.7245	Intermediate Similarity	NPC473456
0.7245	Intermediate Similarity	NPC69385
0.7245	Intermediate Similarity	NPC471815
0.7245	Intermediate Similarity	NPC120299
0.7245	Intermediate Similarity	NPC20066
0.7241	Intermediate Similarity	NPC165711
0.7241	Intermediate Similarity	NPC316324
0.7241	Intermediate Similarity	NPC180290
0.7241	Intermediate Similarity	NPC97377
0.7234	Intermediate Similarity	NPC477973
0.7234	Intermediate Similarity	NPC97577
0.7234	Intermediate Similarity	NPC115179
0.7234	Intermediate Similarity	NPC280833
0.7234	Intermediate Similarity	NPC106040
0.7229	Intermediate Similarity	NPC262673
0.7228	Intermediate Similarity	NPC275583
0.7222	Intermediate Similarity	NPC238991
0.7222	Intermediate Similarity	NPC302661
0.7216	Intermediate Similarity	NPC31021
0.7212	Intermediate Similarity	NPC137911
0.7212	Intermediate Similarity	NPC228477
0.7209	Intermediate Similarity	NPC175079
0.7204	Intermediate Similarity	NPC472007
0.7204	Intermediate Similarity	NPC181327
0.7204	Intermediate Similarity	NPC199382
0.72	Intermediate Similarity	NPC146822
0.72	Intermediate Similarity	NPC206079
0.72	Intermediate Similarity	NPC472643
0.72	Intermediate Similarity	NPC99411
0.7195	Intermediate Similarity	NPC243272
0.7191	Intermediate Similarity	NPC233377
0.7188	Intermediate Similarity	NPC271652
0.7188	Intermediate Similarity	NPC248193
0.7188	Intermediate Similarity	NPC476049
0.7188	Intermediate Similarity	NPC477436
0.7188	Intermediate Similarity	NPC477435
0.7174	Intermediate Similarity	NPC142649
0.7174	Intermediate Similarity	NPC133652
0.7174	Intermediate Similarity	NPC189311
0.7174	Intermediate Similarity	NPC65661
0.7172	Intermediate Similarity	NPC475653
0.7172	Intermediate Similarity	NPC64742
0.7159	Intermediate Similarity	NPC475994
0.7159	Intermediate Similarity	NPC59436
0.7159	Intermediate Similarity	NPC321514
0.7159	Intermediate Similarity	NPC62336
0.7158	Intermediate Similarity	NPC166554
0.7158	Intermediate Similarity	NPC51486
0.7158	Intermediate Similarity	NPC77337
0.7158	Intermediate Similarity	NPC475823
0.7158	Intermediate Similarity	NPC476369
0.7158	Intermediate Similarity	NPC476437
0.7158	Intermediate Similarity	NPC145666
0.7158	Intermediate Similarity	NPC471399
0.7158	Intermediate Similarity	NPC474209
0.7158	Intermediate Similarity	NPC129913
0.7157	Intermediate Similarity	NPC13385
0.7157	Intermediate Similarity	NPC309190
0.7157	Intermediate Similarity	NPC213366
0.7157	Intermediate Similarity	NPC235889
0.7143	Intermediate Similarity	NPC52609
0.7143	Intermediate Similarity	NPC475083
0.7143	Intermediate Similarity	NPC49019
0.7143	Intermediate Similarity	NPC184065
0.7143	Intermediate Similarity	NPC1761
0.7143	Intermediate Similarity	NPC269492
0.7143	Intermediate Similarity	NPC9812
0.7143	Intermediate Similarity	NPC288281
0.7143	Intermediate Similarity	NPC318766
0.7143	Intermediate Similarity	NPC291062
0.7143	Intermediate Similarity	NPC472508
0.7143	Intermediate Similarity	NPC94743
0.7128	Intermediate Similarity	NPC473229
0.7128	Intermediate Similarity	NPC185059
0.7128	Intermediate Similarity	NPC53454
0.7128	Intermediate Similarity	NPC475001
0.7128	Intermediate Similarity	NPC72397
0.7128	Intermediate Similarity	NPC473658
0.7126	Intermediate Similarity	NPC61863
0.7126	Intermediate Similarity	NPC250621
0.7125	Intermediate Similarity	NPC143168
0.7125	Intermediate Similarity	NPC477830
0.7125	Intermediate Similarity	NPC53109
0.7115	Intermediate Similarity	NPC472507
0.7113	Intermediate Similarity	NPC477439
0.7113	Intermediate Similarity	NPC477241
0.7111	Intermediate Similarity	NPC474085
0.7111	Intermediate Similarity	NPC172309
0.7111	Intermediate Similarity	NPC117960
0.7111	Intermediate Similarity	NPC286229
0.7111	Intermediate Similarity	NPC116797
0.7111	Intermediate Similarity	NPC14044
0.7111	Intermediate Similarity	NPC475833
0.7111	Intermediate Similarity	NPC99308
0.7108	Intermediate Similarity	NPC125578
0.7108	Intermediate Similarity	NPC146376
0.7108	Intermediate Similarity	NPC263382

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 NPC470177 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1276
0.2-0.3	3631
0.3-0.4	2734
0.4-0.5	887
0.5-0.6	299
0.6-0.7	157
0.7-0.8	13
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
0.7647	Intermediate Similarity	NPD4756	Discovery
0.7586	Intermediate Similarity	NPD4695	Discontinued
0.7447	Intermediate Similarity	NPD6411	Approved
0.7419	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6101	Approved
0.7234	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5695	Phase 3
0.7128	Intermediate Similarity	NPD6672	Approved
0.7128	Intermediate Similarity	NPD5737	Approved
0.7125	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5279	Phase 3
0.7071	Intermediate Similarity	NPD6084	Phase 2
0.7071	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD5696	Approved
0.6979	Remote Similarity	NPD5692	Phase 3
0.6939	Remote Similarity	NPD7748	Approved
0.6939	Remote Similarity	NPD5282	Discontinued
0.6907	Remote Similarity	NPD6050	Approved
0.6907	Remote Similarity	NPD5694	Approved
0.6869	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7331	Phase 2
0.6867	Remote Similarity	NPD3704	Approved
0.6857	Remote Similarity	NPD5697	Approved
0.6848	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3573	Approved
0.6837	Remote Similarity	NPD5779	Approved
0.6837	Remote Similarity	NPD6399	Phase 3
0.6837	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD8039	Approved
0.6809	Remote Similarity	NPD1696	Phase 3
0.6792	Remote Similarity	NPD6011	Approved
0.6792	Remote Similarity	NPD6899	Approved
0.6792	Remote Similarity	NPD6881	Approved
0.6762	Remote Similarity	NPD5739	Approved
0.6762	Remote Similarity	NPD6675	Approved
0.6762	Remote Similarity	NPD6402	Approved
0.6762	Remote Similarity	NPD7128	Approved
0.6737	Remote Similarity	NPD5330	Approved
0.6737	Remote Similarity	NPD4694	Approved
0.6737	Remote Similarity	NPD6684	Approved
0.6737	Remote Similarity	NPD7334	Approved
0.6737	Remote Similarity	NPD6409	Approved
0.6737	Remote Similarity	NPD5280	Approved
0.6737	Remote Similarity	NPD7146	Approved
0.6737	Remote Similarity	NPD7521	Approved
0.6735	Remote Similarity	NPD7515	Phase 2
0.6735	Remote Similarity	NPD5284	Approved
0.6735	Remote Similarity	NPD5281	Approved
0.6733	Remote Similarity	NPD7902	Approved
0.6729	Remote Similarity	NPD6014	Approved
0.6729	Remote Similarity	NPD6012	Approved
0.6729	Remote Similarity	NPD6013	Approved
0.6701	Remote Similarity	NPD4753	Phase 2
0.6701	Remote Similarity	NPD6080	Approved
0.6701	Remote Similarity	NPD6904	Approved
0.6701	Remote Similarity	NPD6673	Approved
0.6698	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD7320	Approved
0.6634	Remote Similarity	NPD5221	Approved
0.6634	Remote Similarity	NPD5222	Approved
0.6634	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6698	Approved
0.6633	Remote Similarity	NPD46	Approved
0.6633	Remote Similarity	NPD5785	Approved
0.6632	Remote Similarity	NPD1694	Approved
0.6606	Remote Similarity	NPD6847	Approved
0.6606	Remote Similarity	NPD6650	Approved
0.6606	Remote Similarity	NPD6617	Approved
0.6606	Remote Similarity	NPD6869	Approved
0.6606	Remote Similarity	NPD8130	Phase 1
0.6606	Remote Similarity	NPD6649	Approved
0.6598	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6903	Approved
0.6596	Remote Similarity	NPD7154	Phase 3
0.6593	Remote Similarity	NPD3617	Approved
0.6574	Remote Similarity	NPD6372	Approved
0.6574	Remote Similarity	NPD6373	Approved
0.6569	Remote Similarity	NPD5173	Approved
0.6566	Remote Similarity	NPD5693	Phase 1
0.6562	Remote Similarity	NPD6422	Discontinued
0.6562	Remote Similarity	NPD5690	Phase 2
0.6548	Remote Similarity	NPD7341	Phase 2
0.6545	Remote Similarity	NPD8297	Approved
0.6545	Remote Similarity	NPD6882	Approved
0.6535	Remote Similarity	NPD4629	Approved
0.6535	Remote Similarity	NPD5654	Approved
0.6535	Remote Similarity	NPD5210	Approved
0.6526	Remote Similarity	NPD3665	Phase 1
0.6526	Remote Similarity	NPD4197	Approved
0.6526	Remote Similarity	NPD3133	Approved
0.6526	Remote Similarity	NPD3666	Approved
0.6505	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3667	Approved
0.6489	Remote Similarity	NPD6435	Approved
0.6471	Remote Similarity	NPD7839	Suspended
0.6471	Remote Similarity	NPD4697	Phase 3
0.6465	Remote Similarity	NPD5207	Approved
0.6458	Remote Similarity	NPD5363	Approved
0.6458	Remote Similarity	NPD5329	Approved
0.6455	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5286	Approved
0.6442	Remote Similarity	NPD4696	Approved
0.6442	Remote Similarity	NPD5285	Approved
0.6436	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7900	Approved
0.6429	Remote Similarity	NPD4518	Approved
0.6413	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4755	Approved
0.6408	Remote Similarity	NPD5959	Approved
0.64	Remote Similarity	NPD7637	Suspended
0.64	Remote Similarity	NPD6079	Approved
0.64	Remote Similarity	NPD7983	Approved
0.6392	Remote Similarity	NPD3618	Phase 1
0.6392	Remote Similarity	NPD6098	Approved
0.6383	Remote Similarity	NPD5369	Approved
0.6381	Remote Similarity	NPD5223	Approved
0.6372	Remote Similarity	NPD6868	Approved
0.6372	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD5328	Approved
0.6354	Remote Similarity	NPD4786	Approved
0.6354	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4225	Approved
0.6339	Remote Similarity	NPD4632	Approved
0.6321	Remote Similarity	NPD5224	Approved
0.6321	Remote Similarity	NPD5226	Approved
0.6321	Remote Similarity	NPD4633	Approved
0.6321	Remote Similarity	NPD5211	Phase 2
0.6321	Remote Similarity	NPD5225	Approved
0.6316	Remote Similarity	NPD4223	Phase 3
0.6316	Remote Similarity	NPD6317	Approved
0.6316	Remote Similarity	NPD4221	Approved
0.6311	Remote Similarity	NPD7614	Phase 1
0.6311	Remote Similarity	NPD7260	Phase 2
0.63	Remote Similarity	NPD7838	Discovery
0.6286	Remote Similarity	NPD4700	Approved
0.6277	Remote Similarity	NPD5368	Approved
0.6275	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5208	Approved
0.6262	Remote Similarity	NPD5174	Approved
0.6262	Remote Similarity	NPD5175	Approved
0.6261	Remote Similarity	NPD6314	Approved
0.6261	Remote Similarity	NPD6313	Approved
0.6261	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD6110	Phase 1
0.625	Remote Similarity	NPD5362	Discontinued
0.6224	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5786	Approved
0.6216	Remote Similarity	NPD6371	Approved
0.6214	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7101	Approved
0.6207	Remote Similarity	NPD7100	Approved
0.6204	Remote Similarity	NPD5141	Approved
0.619	Remote Similarity	NPD4191	Approved
0.619	Remote Similarity	NPD4194	Approved
0.619	Remote Similarity	NPD4193	Approved
0.619	Remote Similarity	NPD7638	Approved
0.619	Remote Similarity	NPD4192	Approved
0.6186	Remote Similarity	NPD3668	Phase 3
0.6182	Remote Similarity	NPD6686	Approved
0.6176	Remote Similarity	NPD5133	Approved
0.6174	Remote Similarity	NPD6009	Approved
0.6154	Remote Similarity	NPD6319	Approved
0.6154	Remote Similarity	NPD7732	Phase 3
0.6154	Remote Similarity	NPD4058	Approved
0.6147	Remote Similarity	NPD6008	Approved
0.6146	Remote Similarity	NPD4269	Approved
0.6146	Remote Similarity	NPD4270	Approved
0.6139	Remote Similarity	NPD4096	Approved
0.6132	Remote Similarity	NPD7639	Approved
0.6132	Remote Similarity	NPD7640	Approved
0.6111	Remote Similarity	NPD4754	Approved
0.6111	Remote Similarity	NPD5276	Approved
0.6106	Remote Similarity	NPD6053	Discontinued
0.6105	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5983	Phase 2
0.6091	Remote Similarity	NPD6412	Phase 2
0.6091	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4690	Approved
0.6061	Remote Similarity	NPD5205	Approved
0.6061	Remote Similarity	NPD4138	Approved
0.6061	Remote Similarity	NPD4688	Approved
0.6061	Remote Similarity	NPD4689	Approved
0.6061	Remote Similarity	NPD4623	Approved
0.6061	Remote Similarity	NPD4519	Discontinued
0.6061	Remote Similarity	NPD4693	Phase 3
0.6047	Remote Similarity	NPD3197	Phase 1
0.6047	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD4729	Approved
0.6036	Remote Similarity	NPD5128	Approved
0.6036	Remote Similarity	NPD4730	Approved
0.6036	Remote Similarity	NPD5168	Approved
0.6034	Remote Similarity	NPD7115	Discovery
0.6019	Remote Similarity	NPD4202	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