NPASS Compound

Structure

CID200580 OpenBabel06191715592D 26 30 0 0 1 0 0 0 0 0999 V2000 3.0115 -2.0033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9260 -2.1451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6018 -2.7745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3906 -2.3191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8130 -2.3190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8131 -3.2858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6261 -1.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0675 -0.7987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8130 -0.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0955 -2.0033 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6261 -2.8164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0001 -2.8164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.8776 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6018 -0.9528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7518 -1.4081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7912 -0.0618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8130 -0.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3906 -1.4082 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8130 -1.4082 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8130 -1.4081 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7932 -3.2744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2098 -0.6148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1817 0.6151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6018 -0.0139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6971 0.0334 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 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 18 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 8 18 1 0 0 0 0 8 25 1 0 0 0 0 9 19 1 0 0 0 0 9 26 1 0 0 0 0 10 1 1 6 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 6 1 6 0 0 0 12 13 1 0 0 0 0 12 21 1 1 0 0 0 13 19 1 1 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 1 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 17 26 1 0 0 0 0 18 2 1 6 0 0 0 19 5 1 1 0 0 0 20 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	356.526
LogP:	1.767
LogD:	1.721
LogS:	-4.015
# Rotatable Bonds:	0
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.519
Synthetic Accessibility Score:	6.631
Fsp3:	0.85
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:	-5.265
MDCK Permeability:	1.9654167772387154e-05
Pgp-inhibitor:	0.35
Pgp-substrate:	0.545
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.854
Plasma Protein Binding (PPB):	45.138954162597656%
Volume Distribution (VD):	0.924
Pgp-substrate:	56.96381759643555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.927
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.931
CYP3A4-substrate:	0.341

ADMET: Excretion

Clearance (CL):	6.634
Half-life (T1/2):	0.23

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.29
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.443
Maximum Recommended Daily Dose:	0.417
Skin Sensitization:	0.038
Carcinogencity:	0.609
Eye Corrosion:	0.016
Eye Irritation:	0.506
Respiratory Toxicity:	0.634

Download Data

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

Natural Product: NPC200580

Natural Product ID:	NPC200580
*Common Name:**	Guidongnin C
IUPAC Name:	n.a.
Synonyms:	Guidongnin C
Standard InCHIKey:	UJOVIPONWVKELP-BHVIDLPJSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-10-11-6-12(21)13-19(9-26-17(24)20(13,7-11)15(10)22)5-3-4-18(2)8-25-16(23)14(18)19/h10-14,21H,3-9H2,1-2H3/t10-,11-,12-,13+,14-,18+,19-,20+/m1/s1
SMILES:	C[C@@H]1[C@@H]2C[C@H]([C@H]3[C@@]4(CCC[C@@]5(C)COC(=O)[C@@H]45)COC(=O)[C@]3(C2)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462455
PubChem CID:	12067306
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14575445]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20521771]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[524622]

☑ 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 NPC200580 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	395
0.1-0.2	3272
0.2-0.3	8707
0.3-0.4	13916
0.4-0.5	5970
0.5-0.6	5633
0.6-0.7	3746
0.7-0.8	874
0.8-0.85	142
0.85-0.9	24
0.9-0.95	17
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9326	High Similarity	NPC193785
0.8916	High Similarity	NPC1882
0.8837	High Similarity	NPC473350
0.8817	High Similarity	NPC267921
0.8778	High Similarity	NPC476189
0.8721	High Similarity	NPC473336
0.8721	High Similarity	NPC471044
0.8652	High Similarity	NPC471459
0.8652	High Similarity	NPC61688
0.8652	High Similarity	NPC67653
0.8646	High Similarity	NPC88469
0.8587	High Similarity	NPC62407
0.8587	High Similarity	NPC287354
0.8506	High Similarity	NPC477434
0.8478	Intermediate Similarity	NPC470424
0.8409	Intermediate Similarity	NPC477205
0.837	Intermediate Similarity	NPC161035
0.8367	Intermediate Similarity	NPC164600
0.8367	Intermediate Similarity	NPC103172
0.8352	Intermediate Similarity	NPC77756
0.8333	Intermediate Similarity	NPC226491
0.8333	Intermediate Similarity	NPC39683
0.8333	Intermediate Similarity	NPC90676
0.8333	Intermediate Similarity	NPC477614
0.8316	Intermediate Similarity	NPC26270
0.8298	Intermediate Similarity	NPC116683
0.8295	Intermediate Similarity	NPC101138
0.8295	Intermediate Similarity	NPC82492
0.8295	Intermediate Similarity	NPC237938
0.8295	Intermediate Similarity	NPC219535
0.8295	Intermediate Similarity	NPC25802
0.8295	Intermediate Similarity	NPC51135
0.8283	Intermediate Similarity	NPC88833
0.8283	Intermediate Similarity	NPC96333
0.8261	Intermediate Similarity	NPC52756
0.8256	Intermediate Similarity	NPC125366
0.8247	Intermediate Similarity	NPC470172
0.8247	Intermediate Similarity	NPC471254
0.8242	Intermediate Similarity	NPC477443
0.8242	Intermediate Similarity	NPC477440
0.8222	Intermediate Similarity	NPC239938
0.8191	Intermediate Similarity	NPC305808
0.8182	Intermediate Similarity	NPC15091
0.8163	Intermediate Similarity	NPC471253
0.8163	Intermediate Similarity	NPC473406
0.8163	Intermediate Similarity	NPC96217
0.8161	Intermediate Similarity	NPC58631
0.8152	Intermediate Similarity	NPC477433
0.8152	Intermediate Similarity	NPC477442
0.8152	Intermediate Similarity	NPC477444
0.8144	Intermediate Similarity	NPC148279
0.8144	Intermediate Similarity	NPC236585
0.814	Intermediate Similarity	NPC80891
0.814	Intermediate Similarity	NPC320144
0.814	Intermediate Similarity	NPC201276
0.8132	Intermediate Similarity	NPC471221
0.8132	Intermediate Similarity	NPC473319
0.8132	Intermediate Similarity	NPC236459
0.8132	Intermediate Similarity	NPC3032
0.8132	Intermediate Similarity	NPC131104
0.8125	Intermediate Similarity	NPC474793
0.8125	Intermediate Similarity	NPC471038
0.8125	Intermediate Similarity	NPC253995
0.8111	Intermediate Similarity	NPC248216
0.8111	Intermediate Similarity	NPC302111
0.8111	Intermediate Similarity	NPC80700
0.8111	Intermediate Similarity	NPC83242
0.8111	Intermediate Similarity	NPC120395
0.81	Intermediate Similarity	NPC61071
0.809	Intermediate Similarity	NPC50438
0.809	Intermediate Similarity	NPC473299
0.8081	Intermediate Similarity	NPC101842
0.8068	Intermediate Similarity	NPC289486
0.8068	Intermediate Similarity	NPC13494
0.8068	Intermediate Similarity	NPC61107
0.8065	Intermediate Similarity	NPC475878
0.8046	Intermediate Similarity	NPC477851
0.8046	Intermediate Similarity	NPC134227
0.8039	Intermediate Similarity	NPC98069
0.8039	Intermediate Similarity	NPC49730
0.8023	Intermediate Similarity	NPC185465
0.8023	Intermediate Similarity	NPC80089
0.8023	Intermediate Similarity	NPC224802
0.8023	Intermediate Similarity	NPC34046
0.8023	Intermediate Similarity	NPC171426
0.8023	Intermediate Similarity	NPC324700
0.8022	Intermediate Similarity	NPC470920
0.8021	Intermediate Similarity	NPC253586
0.8021	Intermediate Similarity	NPC471241
0.8	Intermediate Similarity	NPC474020
0.8	Intermediate Similarity	NPC471046
0.8	Intermediate Similarity	NPC470232
0.798	Intermediate Similarity	NPC140723
0.798	Intermediate Similarity	NPC139347
0.7979	Intermediate Similarity	NPC472238
0.7979	Intermediate Similarity	NPC472237
0.7978	Intermediate Similarity	NPC268578
0.7978	Intermediate Similarity	NPC217559
0.7978	Intermediate Similarity	NPC292458
0.7976	Intermediate Similarity	NPC477867
0.7959	Intermediate Similarity	NPC178853
0.7959	Intermediate Similarity	NPC46848
0.7957	Intermediate Similarity	NPC475211
0.7957	Intermediate Similarity	NPC88337
0.7955	Intermediate Similarity	NPC475743
0.7917	Intermediate Similarity	NPC476728
0.7917	Intermediate Similarity	NPC200054
0.7917	Intermediate Similarity	NPC329910
0.7917	Intermediate Similarity	NPC29410
0.7912	Intermediate Similarity	NPC472272
0.7907	Intermediate Similarity	NPC477918
0.7907	Intermediate Similarity	NPC169389
0.7907	Intermediate Similarity	NPC207010
0.7907	Intermediate Similarity	NPC317913
0.7895	Intermediate Similarity	NPC475118
0.7895	Intermediate Similarity	NPC470386
0.7895	Intermediate Similarity	NPC309127
0.7895	Intermediate Similarity	NPC470385
0.7895	Intermediate Similarity	NPC470423
0.7895	Intermediate Similarity	NPC247877
0.7889	Intermediate Similarity	NPC319909
0.7882	Intermediate Similarity	NPC159789
0.7882	Intermediate Similarity	NPC125767
0.7882	Intermediate Similarity	NPC21220
0.7879	Intermediate Similarity	NPC275990
0.7879	Intermediate Similarity	NPC124544
0.7879	Intermediate Similarity	NPC244969
0.7879	Intermediate Similarity	NPC213528
0.7872	Intermediate Similarity	NPC474065
0.7872	Intermediate Similarity	NPC250753
0.7865	Intermediate Similarity	NPC100366
0.7865	Intermediate Similarity	NPC242771
0.7865	Intermediate Similarity	NPC164289
0.7865	Intermediate Similarity	NPC311642
0.7865	Intermediate Similarity	NPC121121
0.7857	Intermediate Similarity	NPC470388
0.7857	Intermediate Similarity	NPC108371
0.7857	Intermediate Similarity	NPC474755
0.7849	Intermediate Similarity	NPC24705
0.7849	Intermediate Similarity	NPC56962
0.7843	Intermediate Similarity	NPC232133
0.7835	Intermediate Similarity	NPC472273
0.7826	Intermediate Similarity	NPC263802
0.7822	Intermediate Similarity	NPC285927
0.7812	Intermediate Similarity	NPC98639
0.7812	Intermediate Similarity	NPC470229
0.7812	Intermediate Similarity	NPC17336
0.7802	Intermediate Similarity	NPC477445
0.78	Intermediate Similarity	NPC122811
0.78	Intermediate Similarity	NPC87927
0.78	Intermediate Similarity	NPC107385
0.78	Intermediate Similarity	NPC209298
0.78	Intermediate Similarity	NPC277074
0.7791	Intermediate Similarity	NPC4209
0.7791	Intermediate Similarity	NPC472486
0.7791	Intermediate Similarity	NPC472487
0.7791	Intermediate Similarity	NPC477933
0.7791	Intermediate Similarity	NPC477932
0.7778	Intermediate Similarity	NPC163963
0.7778	Intermediate Similarity	NPC14634
0.7778	Intermediate Similarity	NPC52899
0.7778	Intermediate Similarity	NPC289148
0.7778	Intermediate Similarity	NPC472847
0.7767	Intermediate Similarity	NPC469983
0.7766	Intermediate Similarity	NPC470114
0.7765	Intermediate Similarity	NPC55508
0.7755	Intermediate Similarity	NPC28864
0.7755	Intermediate Similarity	NPC162459
0.7755	Intermediate Similarity	NPC38471
0.7755	Intermediate Similarity	NPC98837
0.7755	Intermediate Similarity	NPC89099
0.7755	Intermediate Similarity	NPC20479
0.7755	Intermediate Similarity	NPC38296
0.7745	Intermediate Similarity	NPC471474
0.7745	Intermediate Similarity	NPC186054
0.7742	Intermediate Similarity	NPC201607
0.7742	Intermediate Similarity	NPC56413
0.7742	Intermediate Similarity	NPC476435
0.7742	Intermediate Similarity	NPC56777
0.7732	Intermediate Similarity	NPC475765
0.7732	Intermediate Similarity	NPC475785
0.7732	Intermediate Similarity	NPC470387
0.7727	Intermediate Similarity	NPC472310
0.7723	Intermediate Similarity	NPC327093
0.7723	Intermediate Similarity	NPC13149
0.7723	Intermediate Similarity	NPC474558
0.7723	Intermediate Similarity	NPC470167
0.7723	Intermediate Similarity	NPC100078
0.7723	Intermediate Similarity	NPC202793
0.7717	Intermediate Similarity	NPC477441
0.7717	Intermediate Similarity	NPC476717
0.7717	Intermediate Similarity	NPC114378
0.7717	Intermediate Similarity	NPC103782
0.7717	Intermediate Similarity	NPC92139
0.7708	Intermediate Similarity	NPC206878
0.7708	Intermediate Similarity	NPC47853
0.7701	Intermediate Similarity	NPC143250
0.7701	Intermediate Similarity	NPC471151
0.7701	Intermediate Similarity	NPC307865
0.77	Intermediate Similarity	NPC148628

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 NPC200580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	422
0.1-0.2	3469
0.2-0.3	3463
0.3-0.4	1082
0.4-0.5	320
0.5-0.6	224
0.6-0.7	140
0.7-0.8	23
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8023	Intermediate Similarity	NPD6697	Approved
0.8023	Intermediate Similarity	NPD6115	Approved
0.8023	Intermediate Similarity	NPD6114	Approved
0.8023	Intermediate Similarity	NPD6118	Approved
0.7907	Intermediate Similarity	NPD6116	Phase 1
0.7882	Intermediate Similarity	NPD3703	Phase 2
0.7791	Intermediate Similarity	NPD6117	Approved
0.7674	Intermediate Similarity	NPD3702	Approved
0.7558	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD1700	Approved
0.7379	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD4224	Phase 2
0.7143	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.7126	Intermediate Similarity	NPD5777	Approved
0.7126	Intermediate Similarity	NPD6081	Approved
0.7093	Intermediate Similarity	NPD3698	Phase 2
0.7065	Intermediate Similarity	NPD6928	Phase 2
0.7011	Intermediate Similarity	NPD4245	Approved
0.7011	Intermediate Similarity	NPD4244	Approved
0.7011	Intermediate Similarity	NPD4789	Approved
0.69	Remote Similarity	NPD6399	Phase 3
0.6875	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7320	Approved
0.6848	Remote Similarity	NPD4802	Phase 2
0.6848	Remote Similarity	NPD4238	Approved
0.6838	Remote Similarity	NPD7492	Approved
0.6822	Remote Similarity	NPD7128	Approved
0.6822	Remote Similarity	NPD6675	Approved
0.6822	Remote Similarity	NPD5739	Approved
0.6822	Remote Similarity	NPD6402	Approved
0.6789	Remote Similarity	NPD6373	Approved
0.6789	Remote Similarity	NPD6372	Approved
0.6783	Remote Similarity	NPD6054	Approved
0.6783	Remote Similarity	NPD6319	Approved
0.6783	Remote Similarity	NPD6059	Approved
0.6782	Remote Similarity	NPD5360	Phase 3
0.6782	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6616	Approved
0.6759	Remote Similarity	NPD5697	Approved
0.6759	Remote Similarity	NPD5701	Approved
0.6724	Remote Similarity	NPD6015	Approved
0.6724	Remote Similarity	NPD6016	Approved
0.6723	Remote Similarity	NPD8293	Discontinued
0.6723	Remote Similarity	NPD7078	Approved
0.6697	Remote Similarity	NPD6899	Approved
0.6697	Remote Similarity	NPD6881	Approved
0.6697	Remote Similarity	NPD6011	Approved
0.6696	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD3671	Phase 1
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6636	Remote Similarity	NPD6012	Approved
0.6636	Remote Similarity	NPD6013	Approved
0.6636	Remote Similarity	NPD6014	Approved
0.6632	Remote Similarity	NPD1779	Approved
0.6632	Remote Similarity	NPD1780	Approved
0.66	Remote Similarity	NPD5328	Approved
0.6591	Remote Similarity	NPD229	Approved
0.6577	Remote Similarity	NPD7290	Approved
0.6577	Remote Similarity	NPD7102	Approved
0.6577	Remote Similarity	NPD6883	Approved
0.6571	Remote Similarity	NPD7638	Approved
0.6556	Remote Similarity	NPD4758	Discontinued
0.6538	Remote Similarity	NPD4697	Phase 3
0.6522	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6009	Approved
0.6518	Remote Similarity	NPD6869	Approved
0.6518	Remote Similarity	NPD6847	Approved
0.6518	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6617	Approved
0.6518	Remote Similarity	NPD8130	Phase 1
0.6509	Remote Similarity	NPD7639	Approved
0.6509	Remote Similarity	NPD7640	Approved
0.6509	Remote Similarity	NPD8418	Phase 2
0.6495	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD3669	Approved
0.6486	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4755	Approved
0.6475	Remote Similarity	NPD7319	Approved
0.6471	Remote Similarity	NPD6079	Approved
0.6465	Remote Similarity	NPD3618	Phase 1
0.646	Remote Similarity	NPD8297	Approved
0.646	Remote Similarity	NPD6882	Approved
0.6442	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5983	Phase 2
0.6441	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6921	Approved
0.6429	Remote Similarity	NPD4634	Approved
0.6422	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD8171	Discontinued
0.6393	Remote Similarity	NPD6033	Approved
0.6389	Remote Similarity	NPD7632	Discontinued
0.6381	Remote Similarity	NPD5222	Approved
0.6381	Remote Similarity	NPD5221	Approved
0.6381	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7507	Approved
0.6355	Remote Similarity	NPD5286	Approved
0.6355	Remote Similarity	NPD4700	Approved
0.6355	Remote Similarity	NPD5285	Approved
0.6355	Remote Similarity	NPD4696	Approved
0.6333	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7604	Phase 2
0.6333	Remote Similarity	NPD8328	Phase 3
0.6321	Remote Similarity	NPD5173	Approved
0.6321	Remote Similarity	NPD7902	Approved
0.6321	Remote Similarity	NPD6084	Phase 2
0.6321	Remote Similarity	NPD6083	Phase 2
0.6316	Remote Similarity	NPD5364	Discontinued
0.6311	Remote Similarity	NPD6411	Approved
0.6306	Remote Similarity	NPD6412	Phase 2
0.63	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5223	Approved
0.6293	Remote Similarity	NPD6274	Approved
0.6293	Remote Similarity	NPD6940	Discontinued
0.6263	Remote Similarity	NPD4786	Approved
0.6262	Remote Similarity	NPD5696	Approved
0.6261	Remote Similarity	NPD8133	Approved
0.625	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4202	Approved
0.6239	Remote Similarity	NPD5211	Phase 2
0.6239	Remote Similarity	NPD5224	Approved
0.6239	Remote Similarity	NPD5226	Approved
0.6239	Remote Similarity	NPD5225	Approved
0.6239	Remote Similarity	NPD7115	Discovery
0.6239	Remote Similarity	NPD4633	Approved
0.6239	Remote Similarity	NPD6317	Approved
0.623	Remote Similarity	NPD6336	Discontinued
0.6224	Remote Similarity	NPD3667	Approved
0.6195	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7748	Approved
0.619	Remote Similarity	NPD6001	Approved
0.6186	Remote Similarity	NPD6314	Approved
0.6186	Remote Similarity	NPD6335	Approved
0.6186	Remote Similarity	NPD6313	Approved
0.6182	Remote Similarity	NPD5175	Approved
0.6182	Remote Similarity	NPD5174	Approved
0.6182	Remote Similarity	NPD4754	Approved
0.6176	Remote Similarity	NPD6672	Approved
0.6176	Remote Similarity	NPD5737	Approved
0.6176	Remote Similarity	NPD6903	Approved
0.6162	Remote Similarity	NPD4788	Approved
0.6154	Remote Similarity	NPD7515	Phase 2
0.6154	Remote Similarity	NPD6868	Approved
0.614	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6684	Approved
0.6139	Remote Similarity	NPD7521	Approved
0.6139	Remote Similarity	NPD5330	Approved
0.6139	Remote Similarity	NPD7334	Approved
0.6139	Remote Similarity	NPD7146	Approved
0.6139	Remote Similarity	NPD6409	Approved
0.6134	Remote Similarity	NPD7100	Approved
0.6134	Remote Similarity	NPD7101	Approved
0.6132	Remote Similarity	NPD7991	Discontinued
0.6132	Remote Similarity	NPD5695	Phase 3
0.6126	Remote Similarity	NPD5141	Approved
0.6117	Remote Similarity	NPD6101	Approved
0.6117	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.61	Remote Similarity	NPD3666	Approved
0.61	Remote Similarity	NPD3665	Phase 1
0.61	Remote Similarity	NPD3133	Approved
0.6077	Remote Similarity	NPD6334	Approved
0.6077	Remote Similarity	NPD6333	Approved
0.6071	Remote Similarity	NPD4767	Approved
0.6071	Remote Similarity	NPD4768	Approved
0.6047	Remote Similarity	NPD3198	Approved
0.6038	Remote Similarity	NPD7900	Approved
0.6038	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5282	Discontinued
0.6034	Remote Similarity	NPD6053	Discontinued
0.6033	Remote Similarity	NPD6909	Approved
0.6033	Remote Similarity	NPD6908	Approved
0.6019	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7518	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD7517	Approved
0.6	Remote Similarity	NPD7519	Approved
0.6	Remote Similarity	NPD5281	Approved
0.5981	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD4730	Approved
0.5965	Remote Similarity	NPD6686	Approved
0.5965	Remote Similarity	NPD4729	Approved
0.5965	Remote Similarity	NPD5128	Approved
0.5963	Remote Similarity	NPD4225	Approved
0.5962	Remote Similarity	NPD4753	Phase 2
0.5943	Remote Similarity	NPD5778	Approved
0.5943	Remote Similarity	NPD5779	Approved
0.5935	Remote Similarity	NPD6067	Discontinued

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