NPASS Compound

Structure

NPC20078 OpenBabel07101718282D 21 23 0 0 1 0 0 0 0 0999 V2000 -0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 1.3660 -0.6340 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 0.0000 -3.0000 0.0000 C 0 0 1 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 1.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -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 2.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 2.7321 -3.0000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 13 2 0 0 0 0 9 12 1 0 0 0 0 9 17 1 1 0 0 0 10 18 2 0 0 0 0 11 15 1 0 0 0 0 11 16 1 1 0 0 0 12 16 1 1 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 16 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.16
Volume:	298.301
LogP:	1.161
LogD:	0.862
LogS:	-2.818
# Rotatable Bonds:	1
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.669
Synthetic Accessibility Score:	5.303
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.783
MDCK Permeability:	4.0719169192016125e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.051
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.622
Plasma Protein Binding (PPB):	64.06114959716797%
Volume Distribution (VD):	0.33
Pgp-substrate:	38.06773376464844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.753
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.268
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.235

ADMET: Excretion

Clearance (CL):	4.785
Half-life (T1/2):	0.686

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.107
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.771
Maximum Recommended Daily Dose:	0.093
Skin Sensitization:	0.106
Carcinogencity:	0.408
Eye Corrosion:	0.004
Eye Irritation:	0.036
Respiratory Toxicity:	0.367

Download Data

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

Natural Product: NPC20078

Natural Product ID:	NPC20078
*Common Name:**	Pestaloficiol D
IUPAC Name:	(2'R,6S,7R,8R)-6,7-dihydroxy-2'-(2-hydroxypropan-2-yl)-2,2-dimethylspiro[3,5,6,7-tetrahydrochromene-8,1'-cyclopropane]-4-one
Synonyms:	Pestaloficiol D
Standard InCHIKey:	UBYATBJSFPEGMT-KHMNTURCSA-N
Standard InCHI:	InChI=1S/C16H24O5/c1-14(2)6-10(18)8-5-9(17)12(19)16(13(8)21-14)7-11(16)15(3,4)20/h9,11-12,17,19-20H,5-7H2,1-4H3/t9-,11-,12-,16+/m0/s1
SMILES:	O[C@H]1CC2=C([C@]3([C@H]1O)C[C@H]3C(O)(C)C)OC(CC2=O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500563
PubChem CID:	25022542
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans

*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
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18468908]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19101157]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19618920]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	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
EC50	1
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	26000.0	nM	PMID[544110]
NPT27	Others	Unspecified		CC50	>	200000.0	nM	PMID[544110]

☑ 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 NPC20078 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	259
0.1-0.2	1734
0.2-0.3	5570
0.3-0.4	9751
0.4-0.5	14298
0.5-0.6	7694
0.6-0.7	3101
0.7-0.8	284
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473574
0.9677	High Similarity	NPC181645
0.871	High Similarity	NPC469464
0.81	Intermediate Similarity	NPC306908
0.789	Intermediate Similarity	NPC247069
0.781	Intermediate Similarity	NPC471332
0.781	Intermediate Similarity	NPC471333
0.7778	Intermediate Similarity	NPC61275
0.7778	Intermediate Similarity	NPC146945
0.7778	Intermediate Similarity	NPC171888
0.7757	Intermediate Similarity	NPC101018
0.7745	Intermediate Similarity	NPC35717
0.7723	Intermediate Similarity	NPC91439
0.7714	Intermediate Similarity	NPC65523
0.7692	Intermediate Similarity	NPC478176
0.7677	Intermediate Similarity	NPC146852
0.7647	Intermediate Similarity	NPC27105
0.7636	Intermediate Similarity	NPC7921
0.7636	Intermediate Similarity	NPC477266
0.7636	Intermediate Similarity	NPC478212
0.7636	Intermediate Similarity	NPC208998
0.7615	Intermediate Similarity	NPC474229
0.7593	Intermediate Similarity	NPC471400
0.7593	Intermediate Similarity	NPC20192
0.7589	Intermediate Similarity	NPC122033
0.7589	Intermediate Similarity	NPC478204
0.7589	Intermediate Similarity	NPC470854
0.7589	Intermediate Similarity	NPC474654
0.7589	Intermediate Similarity	NPC287343
0.7589	Intermediate Similarity	NPC97908
0.7573	Intermediate Similarity	NPC471331
0.7573	Intermediate Similarity	NPC472687
0.7573	Intermediate Similarity	NPC99657
0.7573	Intermediate Similarity	NPC203388
0.7573	Intermediate Similarity	NPC471330
0.757	Intermediate Similarity	NPC202524
0.757	Intermediate Similarity	NPC473165
0.7568	Intermediate Similarity	NPC143268
0.7568	Intermediate Similarity	NPC45218
0.7568	Intermediate Similarity	NPC323821
0.7568	Intermediate Similarity	NPC268238
0.7549	Intermediate Similarity	NPC272411
0.7549	Intermediate Similarity	NPC472734
0.7549	Intermediate Similarity	NPC472733
0.7545	Intermediate Similarity	NPC472002
0.7525	Intermediate Similarity	NPC196227
0.7525	Intermediate Similarity	NPC469819
0.7525	Intermediate Similarity	NPC103527
0.7525	Intermediate Similarity	NPC114162
0.7523	Intermediate Similarity	NPC99760
0.7523	Intermediate Similarity	NPC478209
0.7522	Intermediate Similarity	NPC478205
0.7522	Intermediate Similarity	NPC108581
0.7522	Intermediate Similarity	NPC478206
0.7522	Intermediate Similarity	NPC251310
0.75	Intermediate Similarity	NPC16081
0.75	Intermediate Similarity	NPC207217
0.75	Intermediate Similarity	NPC173686
0.75	Intermediate Similarity	NPC94942
0.7478	Intermediate Similarity	NPC477046
0.7478	Intermediate Similarity	NPC102822
0.7477	Intermediate Similarity	NPC470587
0.7477	Intermediate Similarity	NPC198539
0.7477	Intermediate Similarity	NPC128828
0.7476	Intermediate Similarity	NPC472732
0.7476	Intermediate Similarity	NPC20066
0.7476	Intermediate Similarity	NPC472731
0.7456	Intermediate Similarity	NPC470777
0.7455	Intermediate Similarity	NPC317107
0.7455	Intermediate Similarity	NPC476023
0.7453	Intermediate Similarity	NPC159533
0.7434	Intermediate Similarity	NPC53396
0.7434	Intermediate Similarity	NPC58662
0.7434	Intermediate Similarity	NPC477116
0.7434	Intermediate Similarity	NPC469684
0.7434	Intermediate Similarity	NPC98249
0.7434	Intermediate Similarity	NPC27999
0.7431	Intermediate Similarity	NPC87335
0.7429	Intermediate Similarity	NPC471401
0.7429	Intermediate Similarity	NPC112613
0.7429	Intermediate Similarity	NPC470184
0.7429	Intermediate Similarity	NPC207885
0.7426	Intermediate Similarity	NPC477435
0.7426	Intermediate Similarity	NPC477436
0.7411	Intermediate Similarity	NPC238667
0.7407	Intermediate Similarity	NPC112780
0.7404	Intermediate Similarity	NPC153776
0.7404	Intermediate Similarity	NPC472730
0.7404	Intermediate Similarity	NPC472729
0.7404	Intermediate Similarity	NPC177680
0.7395	Intermediate Similarity	NPC477712
0.7395	Intermediate Similarity	NPC477713
0.7391	Intermediate Similarity	NPC268530
0.7391	Intermediate Similarity	NPC478051
0.7391	Intermediate Similarity	NPC251226
0.7391	Intermediate Similarity	NPC154491
0.7387	Intermediate Similarity	NPC317687
0.7387	Intermediate Similarity	NPC90769
0.7383	Intermediate Similarity	NPC40170
0.7379	Intermediate Similarity	NPC8803
0.7379	Intermediate Similarity	NPC93271
0.7379	Intermediate Similarity	NPC135576
0.7374	Intermediate Similarity	NPC476707
0.7374	Intermediate Similarity	NPC476706
0.7374	Intermediate Similarity	NPC143025
0.7368	Intermediate Similarity	NPC17772
0.7368	Intermediate Similarity	NPC188667
0.7368	Intermediate Similarity	NPC204552
0.7368	Intermediate Similarity	NPC284707
0.7358	Intermediate Similarity	NPC295791
0.7353	Intermediate Similarity	NPC258674
0.7353	Intermediate Similarity	NPC212812
0.7347	Intermediate Similarity	NPC474215
0.7347	Intermediate Similarity	NPC475729
0.7345	Intermediate Similarity	NPC179626
0.7339	Intermediate Similarity	NPC151393
0.7339	Intermediate Similarity	NPC469916
0.7339	Intermediate Similarity	NPC322903
0.7339	Intermediate Similarity	NPC472439
0.7333	Intermediate Similarity	NPC472728
0.7333	Intermediate Similarity	NPC472727
0.7333	Intermediate Similarity	NPC198880
0.7333	Intermediate Similarity	NPC46761
0.7328	Intermediate Similarity	NPC159456
0.7328	Intermediate Similarity	NPC4021
0.7327	Intermediate Similarity	NPC475441
0.7327	Intermediate Similarity	NPC116726
0.7327	Intermediate Similarity	NPC73457
0.7327	Intermediate Similarity	NPC111883
0.7321	Intermediate Similarity	NPC49451
0.7315	Intermediate Similarity	NPC181357
0.7315	Intermediate Similarity	NPC102352
0.7308	Intermediate Similarity	NPC111187
0.7308	Intermediate Similarity	NPC190080
0.7308	Intermediate Similarity	NPC273269
0.7308	Intermediate Similarity	NPC236176
0.7308	Intermediate Similarity	NPC471916
0.7304	Intermediate Similarity	NPC268958
0.73	Intermediate Similarity	NPC473100
0.7297	Intermediate Similarity	NPC469656
0.7297	Intermediate Similarity	NPC469655
0.7297	Intermediate Similarity	NPC474846
0.7297	Intermediate Similarity	NPC471243
0.729	Intermediate Similarity	NPC320294
0.729	Intermediate Similarity	NPC473624
0.729	Intermediate Similarity	NPC159442
0.7282	Intermediate Similarity	NPC279313
0.7282	Intermediate Similarity	NPC477437
0.7282	Intermediate Similarity	NPC477438
0.7282	Intermediate Similarity	NPC200702
0.7282	Intermediate Similarity	NPC91408
0.7281	Intermediate Similarity	NPC55296
0.7281	Intermediate Similarity	NPC474518
0.7273	Intermediate Similarity	NPC478210
0.7264	Intermediate Similarity	NPC97435
0.7257	Intermediate Similarity	NPC80650
0.7257	Intermediate Similarity	NPC472400
0.7257	Intermediate Similarity	NPC117712
0.7257	Intermediate Similarity	NPC261330
0.7248	Intermediate Similarity	NPC3316
0.7248	Intermediate Similarity	NPC144854
0.7241	Intermediate Similarity	NPC112038
0.7238	Intermediate Similarity	NPC300584
0.7232	Intermediate Similarity	NPC474516
0.7232	Intermediate Similarity	NPC42658
0.7232	Intermediate Similarity	NPC269530
0.7228	Intermediate Similarity	NPC472325
0.7228	Intermediate Similarity	NPC134321
0.7228	Intermediate Similarity	NPC473099
0.7228	Intermediate Similarity	NPC128672
0.7227	Intermediate Similarity	NPC225049
0.7227	Intermediate Similarity	NPC293112
0.7222	Intermediate Similarity	NPC96268
0.7222	Intermediate Similarity	NPC475036
0.7217	Intermediate Similarity	NPC106644
0.7217	Intermediate Similarity	NPC240509
0.7216	Intermediate Similarity	NPC185256
0.7212	Intermediate Similarity	NPC94337
0.7212	Intermediate Similarity	NPC279722
0.7207	Intermediate Similarity	NPC478211
0.7203	Intermediate Similarity	NPC469789
0.7203	Intermediate Similarity	NPC11895
0.72	Intermediate Similarity	NPC269677
0.72	Intermediate Similarity	NPC476708
0.7196	Intermediate Similarity	NPC474709
0.7193	Intermediate Similarity	NPC251236
0.7193	Intermediate Similarity	NPC96312
0.7193	Intermediate Similarity	NPC328374
0.7193	Intermediate Similarity	NPC40632
0.7184	Intermediate Similarity	NPC478089
0.7184	Intermediate Similarity	NPC477439
0.7184	Intermediate Similarity	NPC477241
0.7182	Intermediate Similarity	NPC277017
0.7182	Intermediate Similarity	NPC218123
0.7182	Intermediate Similarity	NPC65941
0.7182	Intermediate Similarity	NPC154608
0.7182	Intermediate Similarity	NPC231278
0.7182	Intermediate Similarity	NPC293850
0.7182	Intermediate Similarity	NPC112895
0.7182	Intermediate Similarity	NPC192813

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 NPC20078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	2490
0.2-0.3	3668
0.3-0.4	1821
0.4-0.5	576
0.5-0.6	280
0.6-0.7	44
0.7-0.8	2
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
0.7525	Intermediate Similarity	NPD5282	Discontinued
0.7117	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6371	Approved
0.6903	Remote Similarity	NPD4634	Approved
0.6903	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6411	Approved
0.6807	Remote Similarity	NPD6319	Approved
0.6762	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD5778	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6695	Remote Similarity	NPD7115	Discovery
0.6695	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6639	Remote Similarity	NPD8328	Phase 3
0.6637	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6101	Approved
0.6612	Remote Similarity	NPD6015	Approved
0.6612	Remote Similarity	NPD6016	Approved
0.6581	Remote Similarity	NPD4632	Approved
0.6571	Remote Similarity	NPD46	Approved
0.6571	Remote Similarity	NPD6698	Approved
0.6557	Remote Similarity	NPD5988	Approved
0.6557	Remote Similarity	NPD6370	Approved
0.6549	Remote Similarity	NPD5739	Approved
0.6549	Remote Similarity	NPD6675	Approved
0.6549	Remote Similarity	NPD6402	Approved
0.6549	Remote Similarity	NPD7128	Approved
0.6545	Remote Similarity	NPD4696	Approved
0.6545	Remote Similarity	NPD5286	Approved
0.6545	Remote Similarity	NPD4700	Approved
0.6545	Remote Similarity	NPD5285	Approved
0.6522	Remote Similarity	NPD6373	Approved
0.6522	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6372	Approved
0.6509	Remote Similarity	NPD7983	Approved
0.6505	Remote Similarity	NPD3618	Phase 1
0.6496	Remote Similarity	NPD6053	Discontinued
0.6491	Remote Similarity	NPD6412	Phase 2
0.6491	Remote Similarity	NPD5697	Approved
0.6491	Remote Similarity	NPD5701	Approved
0.6484	Remote Similarity	NPD7341	Phase 2
0.6476	Remote Similarity	NPD5328	Approved
0.6455	Remote Similarity	NPD4225	Approved
0.6452	Remote Similarity	NPD7492	Approved
0.6436	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6881	Approved
0.6435	Remote Similarity	NPD6899	Approved
0.6435	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD5224	Approved
0.6429	Remote Similarity	NPD5226	Approved
0.6429	Remote Similarity	NPD5211	Phase 2
0.6429	Remote Similarity	NPD4633	Approved
0.6429	Remote Similarity	NPD5225	Approved
0.6422	Remote Similarity	NPD4697	Phase 3
0.641	Remote Similarity	NPD6649	Approved
0.641	Remote Similarity	NPD6650	Approved
0.64	Remote Similarity	NPD6616	Approved
0.6379	Remote Similarity	NPD6014	Approved
0.6379	Remote Similarity	NPD6012	Approved
0.6379	Remote Similarity	NPD6013	Approved
0.6373	Remote Similarity	NPD6110	Phase 1
0.6372	Remote Similarity	NPD5174	Approved
0.6372	Remote Similarity	NPD5175	Approved
0.6371	Remote Similarity	NPD7604	Phase 2
0.6364	Remote Similarity	NPD7902	Approved
0.6356	Remote Similarity	NPD8297	Approved
0.6355	Remote Similarity	NPD6079	Approved
0.6349	Remote Similarity	NPD8293	Discontinued
0.6349	Remote Similarity	NPD7078	Approved
0.6346	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD8513	Phase 3
0.6339	Remote Similarity	NPD5344	Discontinued
0.6339	Remote Similarity	NPD5223	Approved
0.6325	Remote Similarity	NPD7290	Approved
0.6325	Remote Similarity	NPD6883	Approved
0.6325	Remote Similarity	NPD7102	Approved
0.6316	Remote Similarity	NPD5141	Approved
0.6299	Remote Similarity	NPD7736	Approved
0.6296	Remote Similarity	NPD4202	Approved
0.6296	Remote Similarity	NPD6399	Phase 3
0.6293	Remote Similarity	NPD6011	Approved
0.629	Remote Similarity	NPD8080	Discontinued
0.6281	Remote Similarity	NPD6009	Approved
0.6275	Remote Similarity	NPD3667	Approved
0.6273	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5221	Approved
0.6273	Remote Similarity	NPD5222	Approved
0.6271	Remote Similarity	NPD6847	Approved
0.6271	Remote Similarity	NPD6869	Approved
0.6271	Remote Similarity	NPD6617	Approved
0.6271	Remote Similarity	NPD8130	Phase 1
0.6261	Remote Similarity	NPD4768	Approved
0.6261	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD7319	Approved
0.6239	Remote Similarity	NPD7748	Approved
0.6238	Remote Similarity	NPD4695	Discontinued
0.6237	Remote Similarity	NPD3704	Approved
0.6228	Remote Similarity	NPD4754	Approved
0.6218	Remote Similarity	NPD6882	Approved
0.6216	Remote Similarity	NPD5173	Approved
0.621	Remote Similarity	NPD8516	Approved
0.621	Remote Similarity	NPD8515	Approved
0.621	Remote Similarity	NPD6921	Approved
0.621	Remote Similarity	NPD5983	Phase 2
0.621	Remote Similarity	NPD8517	Approved
0.6207	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7515	Phase 2
0.6172	Remote Similarity	NPD6033	Approved
0.6168	Remote Similarity	NPD4753	Phase 2
0.6154	Remote Similarity	NPD4729	Approved
0.6154	Remote Similarity	NPD3665	Phase 1
0.6154	Remote Similarity	NPD6686	Approved
0.6154	Remote Similarity	NPD5128	Approved
0.6154	Remote Similarity	NPD3666	Approved
0.6154	Remote Similarity	NPD4786	Approved
0.6154	Remote Similarity	NPD4730	Approved
0.6154	Remote Similarity	NPD3133	Approved
0.6148	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD1696	Phase 3
0.6091	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7900	Approved
0.608	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6084	Phase 2
0.6071	Remote Similarity	NPD6083	Phase 2
0.6066	Remote Similarity	NPD6274	Approved
0.6064	Remote Similarity	NPD7331	Phase 2
0.605	Remote Similarity	NPD5247	Approved
0.605	Remote Similarity	NPD5251	Approved
0.605	Remote Similarity	NPD5249	Phase 3
0.605	Remote Similarity	NPD5250	Approved
0.605	Remote Similarity	NPD5248	Approved
0.604	Remote Similarity	NPD3617	Approved
0.6038	Remote Similarity	NPD5279	Phase 3
0.6036	Remote Similarity	NPD5695	Phase 3
0.6036	Remote Similarity	NPD4629	Approved
0.6036	Remote Similarity	NPD5210	Approved
0.6019	Remote Similarity	NPD5369	Approved
0.6018	Remote Similarity	NPD5696	Approved
0.6018	Remote Similarity	NPD7638	Approved
0.6016	Remote Similarity	NPD7507	Approved
0.6016	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD5215	Approved
0.6	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5216	Approved
0.6	Remote Similarity	NPD5217	Approved
0.5981	Remote Similarity	NPD7524	Approved
0.5981	Remote Similarity	NPD3573	Approved
0.5969	Remote Similarity	NPD8074	Phase 3
0.5965	Remote Similarity	NPD6648	Approved
0.5965	Remote Similarity	NPD7639	Approved
0.5965	Remote Similarity	NPD7640	Approved
0.5963	Remote Similarity	NPD7838	Discovery
0.5963	Remote Similarity	NPD5785	Approved
0.5962	Remote Similarity	NPD6435	Approved
0.5943	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD1694	Approved
0.592	Remote Similarity	NPD7101	Approved
0.592	Remote Similarity	NPD4522	Approved
0.592	Remote Similarity	NPD7100	Approved
0.5917	Remote Similarity	NPD5135	Approved
0.5917	Remote Similarity	NPD5169	Approved
0.5917	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD1700	Approved
0.5909	Remote Similarity	NPD7637	Suspended
0.5905	Remote Similarity	NPD6695	Phase 3
0.5893	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5786	Approved
0.5887	Remote Similarity	NPD6317	Approved
0.5868	Remote Similarity	NPD5127	Approved
0.5868	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7632	Discontinued
0.5859	Remote Similarity	NPD7642	Approved
0.5849	Remote Similarity	NPD3668	Phase 3
0.5841	Remote Similarity	NPD7839	Suspended
0.584	Remote Similarity	NPD6313	Approved
0.584	Remote Similarity	NPD6335	Approved
0.584	Remote Similarity	NPD6314	Approved
0.5827	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD6908	Approved
0.5827	Remote Similarity	NPD6909	Approved
0.5818	Remote Similarity	NPD3168	Discontinued
0.581	Remote Similarity	NPD4221	Approved
0.581	Remote Similarity	NPD4223	Phase 3
0.5794	Remote Similarity	NPD5363	Approved
0.5769	Remote Similarity	NPD5368	Approved
0.5766	Remote Similarity	NPD5281	Approved
0.5766	Remote Similarity	NPD5284	Approved
0.5755	Remote Similarity	NPD7154	Phase 3
0.575	Remote Similarity	NPD5168	Approved
0.5743	Remote Similarity	NPD3703	Phase 2
0.5741	Remote Similarity	NPD4249	Approved
0.5741	Remote Similarity	NPD7521	Approved
0.5741	Remote Similarity	NPD5330	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