NPASS Compound

Structure

NPC163685 OpenBabel07101718322D 35 41 0 0 1 0 0 0 0 0999 V2000 0.7798 -3.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7558 -3.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3154 3.0411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2914 3.0411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9582 -0.2440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4226 1.7079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4226 1.2200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6486 0.7320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8034 0.2440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1130 -2.1959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4226 0.7320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1130 -1.2200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2678 0.2440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2678 1.7079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4226 -2.1959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1130 2.1959 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4226 -1.2200 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6486 1.7079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1130 -0.7320 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9582 1.7079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1130 0.2440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2678 -1.2200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8452 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2678 -2.6839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8034 2.1959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9582 0.7320 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2678 0.7320 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4226 0.2440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2678 -0.7320 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4226 -0.7320 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1130 3.1719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4938 2.1959 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3332 0.8452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1130 -1.7079 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 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 26 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 28 1 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 20 1 0 0 0 0 16 31 1 6 0 0 0 17 29 1 1 0 0 0 17 30 1 0 0 0 0 18 25 1 0 0 0 0 18 32 2 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 19 34 1 1 0 0 0 20 25 1 0 0 0 0 20 26 1 6 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 30 1 1 0 0 0 22 34 1 0 0 0 0 23 29 1 0 0 0 0 23 33 2 0 0 0 0 23 35 1 0 0 0 0 26 5 1 6 0 0 0 27 28 1 1 0 0 0 28 30 1 1 0 0 0 29 12 1 6 0 0 0 30 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.32
Volume:	506.219
LogP:	4.769
LogD:	4.017
LogS:	-5.605
# Rotatable Bonds:	0
TPSA:	76.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.384
Synthetic Accessibility Score:	6.599
Fsp3:	0.933
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:	-5.35
MDCK Permeability:	2.3274425984709524e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.669
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.592
Plasma Protein Binding (PPB):	83.87480926513672%
Volume Distribution (VD):	1.142
Pgp-substrate:	15.33719253540039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.762
CYP2C19-inhibitor:	0.092
CYP2C19-substrate:	0.899
CYP2C9-inhibitor:	0.215
CYP2C9-substrate:	0.134
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.865
CYP3A4-substrate:	0.444

ADMET: Excretion

Clearance (CL):	14.844
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.604
Human Hepatotoxicity (H-HT):	0.638
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.78
Skin Sensitization:	0.062
Carcinogencity:	0.342
Eye Corrosion:	0.01
Eye Irritation:	0.017
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC163685

Natural Product ID:	NPC163685
*Common Name:**	BJHPXVYFOSPVSF-PQYJJHRASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BJHPXVYFOSPVSF-PQYJJHRASA-N
Standard InCHI:	InChI=1S/C30H44O5/c1-24(2)10-12-29-13-11-28(7)27(6)14-16(31)20-25(3,4)18(32)8-9-26(20,5)21(27)19-22(34-19)30(28,17(29)15-24)35-23(29)33/h16-17,19-22,31H,8-15H2,1-7H3/t16-,17-,19+,20+,21-,22+,26+,27-,28+,29+,30-/m1/s1
SMILES:	CC1(C)CC[C@]23CC[C@@]4(C)[C@]5(C)C[C@H]([C@H]6C(C)(C)C(=O)CC[C@]6(C)[C@H]5[C@H]5[C@@H]([C@@]4([C@@H]2C1)OC3=O)O5)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501175
PubChem CID:	11591179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	resin	n.a.	n.a.	PMID[16724846]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12830	Styrax tonkinensis	Species	Styracaceae	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IG50	=	41.8	uM	PMID[558010]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	<	10.0	%	PMID[558010]

☑ 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 NPC163685 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	487
0.1-0.2	3606
0.2-0.3	8472
0.3-0.4	14155
0.4-0.5	6314
0.5-0.6	4897
0.6-0.7	3684
0.7-0.8	975
0.8-0.85	83
0.85-0.9	16
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC82633
0.9778	High Similarity	NPC235109
0.9222	High Similarity	NPC472146
0.9222	High Similarity	NPC185529
0.8947	High Similarity	NPC472144
0.8842	High Similarity	NPC472145
0.8713	High Similarity	NPC154906
0.8602	High Similarity	NPC50443
0.8602	High Similarity	NPC18536
0.8587	High Similarity	NPC476435
0.8587	High Similarity	NPC476379
0.8571	High Similarity	NPC83242
0.8556	High Similarity	NPC473299
0.8495	Intermediate Similarity	NPC67653
0.8495	Intermediate Similarity	NPC471459
0.8462	Intermediate Similarity	NPC62572
0.8427	Intermediate Similarity	NPC280781
0.8427	Intermediate Similarity	NPC476071
0.8427	Intermediate Similarity	NPC48756
0.8421	Intermediate Similarity	NPC472148
0.8421	Intermediate Similarity	NPC472147
0.8404	Intermediate Similarity	NPC470114
0.8352	Intermediate Similarity	NPC237938
0.8352	Intermediate Similarity	NPC219535
0.8352	Intermediate Similarity	NPC477434
0.8333	Intermediate Similarity	NPC477495
0.828	Intermediate Similarity	NPC470920
0.8261	Intermediate Similarity	NPC477445
0.8242	Intermediate Similarity	NPC227170
0.8229	Intermediate Similarity	NPC474379
0.8211	Intermediate Similarity	NPC475211
0.8211	Intermediate Similarity	NPC88337
0.8208	Intermediate Similarity	NPC97002
0.8191	Intermediate Similarity	NPC3032
0.8191	Intermediate Similarity	NPC473319
0.8191	Intermediate Similarity	NPC131104
0.8163	Intermediate Similarity	NPC475765
0.8163	Intermediate Similarity	NPC475785
0.8152	Intermediate Similarity	NPC105895
0.8152	Intermediate Similarity	NPC34984
0.8152	Intermediate Similarity	NPC25037
0.8137	Intermediate Similarity	NPC327093
0.8113	Intermediate Similarity	NPC477489
0.8105	Intermediate Similarity	NPC61688
0.8095	Intermediate Similarity	NPC470622
0.8061	Intermediate Similarity	NPC17336
0.8043	Intermediate Similarity	NPC15091
0.8043	Intermediate Similarity	NPC269684
0.8039	Intermediate Similarity	NPC225238
0.8039	Intermediate Similarity	NPC34562
0.8022	Intermediate Similarity	NPC50658
0.8	Intermediate Similarity	NPC477614
0.8	Intermediate Similarity	NPC471221
0.8	Intermediate Similarity	NPC226491
0.8	Intermediate Similarity	NPC73013
0.7981	Intermediate Similarity	NPC126753
0.798	Intermediate Similarity	NPC116683
0.7979	Intermediate Similarity	NPC80700
0.7979	Intermediate Similarity	NPC474215
0.7979	Intermediate Similarity	NPC475729
0.7978	Intermediate Similarity	NPC112463
0.7959	Intermediate Similarity	NPC247877
0.7959	Intermediate Similarity	NPC309127
0.7941	Intermediate Similarity	NPC80640
0.7941	Intermediate Similarity	NPC471254
0.7938	Intermediate Similarity	NPC216137
0.7938	Intermediate Similarity	NPC475878
0.7935	Intermediate Similarity	NPC61107
0.7935	Intermediate Similarity	NPC289486
0.7921	Intermediate Similarity	NPC80417
0.7917	Intermediate Similarity	NPC477440
0.7917	Intermediate Similarity	NPC24705
0.7917	Intermediate Similarity	NPC56962
0.7917	Intermediate Similarity	NPC477443
0.7912	Intermediate Similarity	NPC472951
0.7912	Intermediate Similarity	NPC472943
0.7905	Intermediate Similarity	NPC316930
0.79	Intermediate Similarity	NPC266417
0.79	Intermediate Similarity	NPC471241
0.7889	Intermediate Similarity	NPC31031
0.7889	Intermediate Similarity	NPC472608
0.7889	Intermediate Similarity	NPC243594
0.7879	Intermediate Similarity	NPC62407
0.7879	Intermediate Similarity	NPC470031
0.7879	Intermediate Similarity	NPC287354
0.7872	Intermediate Similarity	NPC477205
0.7872	Intermediate Similarity	NPC131350
0.7872	Intermediate Similarity	NPC473350
0.7857	Intermediate Similarity	NPC476189
0.7835	Intermediate Similarity	NPC477442
0.7835	Intermediate Similarity	NPC477433
0.7835	Intermediate Similarity	NPC77756
0.7835	Intermediate Similarity	NPC477444
0.783	Intermediate Similarity	NPC87393
0.783	Intermediate Similarity	NPC310546
0.783	Intermediate Similarity	NPC320475
0.783	Intermediate Similarity	NPC321661
0.7826	Intermediate Similarity	NPC474870
0.7826	Intermediate Similarity	NPC475743
0.7826	Intermediate Similarity	NPC271572
0.7812	Intermediate Similarity	NPC236459
0.78	Intermediate Similarity	NPC477264
0.78	Intermediate Similarity	NPC256227
0.7789	Intermediate Similarity	NPC302111
0.7789	Intermediate Similarity	NPC476717
0.7789	Intermediate Similarity	NPC248216
0.7789	Intermediate Similarity	NPC228593
0.7789	Intermediate Similarity	NPC235196
0.7788	Intermediate Similarity	NPC100078
0.7788	Intermediate Similarity	NPC301787
0.7788	Intermediate Similarity	NPC267637
0.7778	Intermediate Similarity	NPC470424
0.7778	Intermediate Similarity	NPC470423
0.7778	Intermediate Similarity	NPC157571
0.7778	Intermediate Similarity	NPC143250
0.7778	Intermediate Similarity	NPC477492
0.7767	Intermediate Similarity	NPC244969
0.7767	Intermediate Similarity	NPC470172
0.7767	Intermediate Similarity	NPC213528
0.7766	Intermediate Similarity	NPC9060
0.7766	Intermediate Similarity	NPC473336
0.7766	Intermediate Similarity	NPC181871
0.7766	Intermediate Similarity	NPC471044
0.7757	Intermediate Similarity	NPC66513
0.7757	Intermediate Similarity	NPC471431
0.7755	Intermediate Similarity	NPC52756
0.7742	Intermediate Similarity	NPC477447
0.7742	Intermediate Similarity	NPC470155
0.7742	Intermediate Similarity	NPC477446
0.7736	Intermediate Similarity	NPC207693
0.7723	Intermediate Similarity	NPC472273
0.7717	Intermediate Similarity	NPC125366
0.7714	Intermediate Similarity	NPC273189
0.7714	Intermediate Similarity	NPC138908
0.7714	Intermediate Similarity	NPC158367
0.7714	Intermediate Similarity	NPC166079
0.7714	Intermediate Similarity	NPC470587
0.7714	Intermediate Similarity	NPC158051
0.7714	Intermediate Similarity	NPC119628
0.7714	Intermediate Similarity	NPC184805
0.7714	Intermediate Similarity	NPC200957
0.7714	Intermediate Similarity	NPC222833
0.7714	Intermediate Similarity	NPC306776
0.7708	Intermediate Similarity	NPC202937
0.7708	Intermediate Similarity	NPC239938
0.7708	Intermediate Similarity	NPC263802
0.7692	Intermediate Similarity	NPC26029
0.7692	Intermediate Similarity	NPC471253
0.7692	Intermediate Similarity	NPC473406
0.7684	Intermediate Similarity	NPC476715
0.7684	Intermediate Similarity	NPC474572
0.7677	Intermediate Similarity	NPC475307
0.767	Intermediate Similarity	NPC252614
0.7667	Intermediate Similarity	NPC108840
0.7664	Intermediate Similarity	NPC22709
0.7647	Intermediate Similarity	NPC20479
0.7647	Intermediate Similarity	NPC98837
0.7647	Intermediate Similarity	NPC475876
0.7647	Intermediate Similarity	NPC28864
0.7647	Intermediate Similarity	NPC38296
0.7647	Intermediate Similarity	NPC162459
0.7647	Intermediate Similarity	NPC38471
0.7647	Intermediate Similarity	NPC474724
0.7642	Intermediate Similarity	NPC475630
0.7642	Intermediate Similarity	NPC40716
0.7642	Intermediate Similarity	NPC471430
0.7642	Intermediate Similarity	NPC166993
0.7642	Intermediate Similarity	NPC203974
0.7642	Intermediate Similarity	NPC475234
0.7642	Intermediate Similarity	NPC138219
0.764	Intermediate Similarity	NPC55508
0.764	Intermediate Similarity	NPC159325
0.764	Intermediate Similarity	NPC168511
0.7636	Intermediate Similarity	NPC477465
0.7634	Intermediate Similarity	NPC470154
0.7634	Intermediate Similarity	NPC58631
0.7634	Intermediate Similarity	NPC470156
0.7624	Intermediate Similarity	NPC476728
0.7619	Intermediate Similarity	NPC328737
0.7615	Intermediate Similarity	NPC476964
0.7609	Intermediate Similarity	NPC80891
0.7609	Intermediate Similarity	NPC320144
0.7609	Intermediate Similarity	NPC201276
0.7604	Intermediate Similarity	NPC215968
0.7604	Intermediate Similarity	NPC472272
0.7604	Intermediate Similarity	NPC155531
0.7604	Intermediate Similarity	NPC92139
0.7582	Intermediate Similarity	NPC307865
0.7579	Intermediate Similarity	NPC50438
0.7579	Intermediate Similarity	NPC475689
0.7579	Intermediate Similarity	NPC65133
0.7573	Intermediate Similarity	NPC477656
0.7573	Intermediate Similarity	NPC477655
0.7573	Intermediate Similarity	NPC293866
0.757	Intermediate Similarity	NPC471626
0.757	Intermediate Similarity	NPC469826
0.757	Intermediate Similarity	NPC273155
0.757	Intermediate Similarity	NPC231566
0.757	Intermediate Similarity	NPC262567
0.757	Intermediate Similarity	NPC473688

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 NPC163685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	514
0.1-0.2	3638
0.2-0.3	3339
0.3-0.4	1012
0.4-0.5	331
0.5-0.6	211
0.6-0.7	94
0.7-0.8	11
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
0.75	Intermediate Similarity	NPD6114	Approved
0.75	Intermediate Similarity	NPD6118	Approved
0.75	Intermediate Similarity	NPD6115	Approved
0.75	Intermediate Similarity	NPD6697	Approved
0.7407	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3703	Phase 2
0.7333	Intermediate Similarity	NPD1700	Approved
0.729	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6117	Approved
0.7204	Intermediate Similarity	NPD6116	Phase 1
0.7065	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD8034	Phase 2
0.6893	Remote Similarity	NPD8035	Phase 2
0.6848	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7748	Approved
0.6731	Remote Similarity	NPD7515	Phase 2
0.6729	Remote Similarity	NPD7902	Approved
0.6696	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD5777	Approved
0.6638	Remote Similarity	NPD8133	Approved
0.6632	Remote Similarity	NPD3702	Approved
0.6607	Remote Similarity	NPD6008	Approved
0.6559	Remote Similarity	NPD4245	Approved
0.6559	Remote Similarity	NPD4244	Approved
0.6522	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5360	Phase 3
0.6489	Remote Similarity	NPD6081	Approved
0.6484	Remote Similarity	NPD4224	Phase 2
0.648	Remote Similarity	NPD7736	Approved
0.6471	Remote Similarity	NPD7115	Discovery
0.646	Remote Similarity	NPD6675	Approved
0.646	Remote Similarity	NPD5739	Approved
0.646	Remote Similarity	NPD6402	Approved
0.646	Remote Similarity	NPD7128	Approved
0.6452	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3698	Phase 2
0.6449	Remote Similarity	NPD7900	Approved
0.6449	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6372	Approved
0.6435	Remote Similarity	NPD6373	Approved
0.641	Remote Similarity	NPD8297	Approved
0.64	Remote Similarity	NPD1779	Approved
0.64	Remote Similarity	NPD1780	Approved
0.6383	Remote Similarity	NPD4789	Approved
0.6371	Remote Similarity	NPD7492	Approved
0.6364	Remote Similarity	NPD7638	Approved
0.6356	Remote Similarity	NPD4632	Approved
0.6355	Remote Similarity	NPD8171	Discontinued
0.6348	Remote Similarity	NPD6899	Approved
0.6348	Remote Similarity	NPD6881	Approved
0.6348	Remote Similarity	NPD7320	Approved
0.6325	Remote Similarity	NPD6649	Approved
0.6325	Remote Similarity	NPD6650	Approved
0.632	Remote Similarity	NPD6616	Approved
0.632	Remote Similarity	NPD7507	Approved
0.6311	Remote Similarity	NPD6054	Approved
0.6311	Remote Similarity	NPD6319	Approved
0.6311	Remote Similarity	NPD6059	Approved
0.6306	Remote Similarity	NPD7639	Approved
0.6306	Remote Similarity	NPD7640	Approved
0.63	Remote Similarity	NPD6928	Phase 2
0.6299	Remote Similarity	NPD7319	Approved
0.629	Remote Similarity	NPD7604	Phase 2
0.6275	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD3669	Approved
0.627	Remote Similarity	NPD7078	Approved
0.627	Remote Similarity	NPD8293	Discontinued
0.6263	Remote Similarity	NPD3671	Phase 1
0.6261	Remote Similarity	NPD5697	Approved
0.6261	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD6940	Discontinued
0.6239	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD7290	Approved
0.621	Remote Similarity	NPD6370	Approved
0.6204	Remote Similarity	NPD6399	Phase 3
0.6198	Remote Similarity	NPD6009	Approved
0.6196	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7632	Discontinued
0.6186	Remote Similarity	NPD6617	Approved
0.6186	Remote Similarity	NPD6847	Approved
0.6186	Remote Similarity	NPD6869	Approved
0.6186	Remote Similarity	NPD8130	Phase 1
0.6161	Remote Similarity	NPD8418	Phase 2
0.6154	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6146	Remote Similarity	NPD4758	Discontinued
0.6134	Remote Similarity	NPD6882	Approved
0.6129	Remote Similarity	NPD5983	Phase 2
0.6129	Remote Similarity	NPD6016	Approved
0.6129	Remote Similarity	NPD6015	Approved
0.6121	Remote Similarity	NPD6412	Phase 2
0.61	Remote Similarity	NPD5364	Discontinued
0.6087	Remote Similarity	NPD371	Approved
0.608	Remote Similarity	NPD5988	Approved
0.6075	Remote Similarity	NPD5328	Approved
0.6068	Remote Similarity	NPD6011	Approved
0.6063	Remote Similarity	NPD6336	Discontinued
0.605	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4755	Approved
0.5982	Remote Similarity	NPD6083	Phase 2
0.5982	Remote Similarity	NPD6084	Phase 2
0.5968	Remote Similarity	NPD7516	Approved
0.5963	Remote Similarity	NPD6079	Approved
0.5946	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD3618	Phase 1
0.5932	Remote Similarity	NPD6686	Approved
0.5929	Remote Similarity	NPD4225	Approved
0.5893	Remote Similarity	NPD4697	Phase 3
0.5888	Remote Similarity	NPD3573	Approved
0.5887	Remote Similarity	NPD7327	Approved
0.5887	Remote Similarity	NPD7328	Approved
0.5882	Remote Similarity	NPD7645	Phase 2
0.5877	Remote Similarity	NPD4700	Approved
0.5877	Remote Similarity	NPD5286	Approved
0.5877	Remote Similarity	NPD4696	Approved
0.5877	Remote Similarity	NPD5285	Approved
0.5873	Remote Similarity	NPD8296	Approved
0.5873	Remote Similarity	NPD8335	Approved
0.5873	Remote Similarity	NPD8517	Approved
0.5873	Remote Similarity	NPD8379	Approved
0.5873	Remote Similarity	NPD8513	Phase 3
0.5873	Remote Similarity	NPD8380	Approved
0.5873	Remote Similarity	NPD8378	Approved
0.5873	Remote Similarity	NPD8516	Approved
0.5873	Remote Similarity	NPD8515	Approved
0.5854	Remote Similarity	NPD6274	Approved
0.5846	Remote Similarity	NPD6033	Approved
0.584	Remote Similarity	NPD7100	Approved
0.584	Remote Similarity	NPD7101	Approved
0.5833	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4634	Approved
0.5818	Remote Similarity	NPD6411	Approved
0.581	Remote Similarity	NPD4788	Approved
0.5794	Remote Similarity	NPD8377	Approved
0.5794	Remote Similarity	NPD8294	Approved
0.5789	Remote Similarity	NPD5696	Approved
0.5784	Remote Similarity	NPD4802	Phase 2
0.5784	Remote Similarity	NPD4238	Approved
0.5776	Remote Similarity	NPD5224	Approved
0.5776	Remote Similarity	NPD5225	Approved
0.5776	Remote Similarity	NPD5211	Phase 2
0.5776	Remote Similarity	NPD4633	Approved
0.5776	Remote Similarity	NPD5226	Approved
0.5763	Remote Similarity	NPD6920	Discontinued
0.576	Remote Similarity	NPD6335	Approved
0.5755	Remote Similarity	NPD4786	Approved
0.5752	Remote Similarity	NPD5222	Approved
0.5752	Remote Similarity	NPD5221	Approved
0.5752	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD6909	Approved
0.5748	Remote Similarity	NPD8033	Approved
0.5748	Remote Similarity	NPD6908	Approved
0.5748	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD7909	Approved
0.5726	Remote Similarity	NPD6868	Approved
0.5726	Remote Similarity	NPD5175	Approved
0.5726	Remote Similarity	NPD5174	Approved
0.5714	Remote Similarity	NPD4787	Phase 1
0.5714	Remote Similarity	NPD3667	Approved
0.5702	Remote Similarity	NPD5173	Approved
0.57	Remote Similarity	NPD1810	Approved
0.57	Remote Similarity	NPD1811	Approved
0.569	Remote Similarity	NPD5223	Approved
0.569	Remote Similarity	NPD5344	Discontinued
0.568	Remote Similarity	NPD6317	Approved
0.5678	Remote Similarity	NPD5141	Approved
0.5678	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.567	Remote Similarity	NPD229	Approved
0.5664	Remote Similarity	NPD5695	Phase 3
0.5659	Remote Similarity	NPD6067	Discontinued
0.5648	Remote Similarity	NPD7334	Approved
0.5648	Remote Similarity	NPD6409	Approved
0.5648	Remote Similarity	NPD6684	Approved
0.5648	Remote Similarity	NPD5330	Approved
0.5648	Remote Similarity	NPD7521	Approved
0.5648	Remote Similarity	NPD7146	Approved
0.5641	Remote Similarity	NPD8139	Approved
0.5641	Remote Similarity	NPD8083	Approved
0.5641	Remote Similarity	NPD8082	Approved
0.5641	Remote Similarity	NPD8086	Approved
0.5641	Remote Similarity	NPD8085	Approved
0.5641	Remote Similarity	NPD8138	Approved
0.5641	Remote Similarity	NPD8084	Approved
0.5636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6101	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