NPASS Compound

Structure

NPC470076 OpenBabel07101718232D 37 42 0 0 1 0 0 0 0 0999 V2000 -4.6894 2.3430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9577 -0.5902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6379 0.1428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1285 -1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4044 -1.7702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4022 1.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0932 0.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3972 2.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7170 1.4888 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 -0.8660 0.5000 0.0000 C 0 0 0 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 -4.3804 1.3920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4752 -1.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7624 -0.5102 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3944 2.1472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0495 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6629 0.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4533 -1.4612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 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 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8944 3.0132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0277 0.8567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6613 -2.4394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7405 -0.3023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9577 1.3209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 7 8 1 0 0 0 0 7 16 2 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 12 2 0 0 0 0 10 22 1 0 0 0 0 11 26 1 0 0 0 0 12 29 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 29 1 0 0 0 0 15 30 1 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 17 31 1 1 0 0 0 18 27 1 6 0 0 0 18 28 1 0 0 0 0 19 26 1 1 0 0 0 19 30 1 0 0 0 0 20 27 1 1 0 0 0 20 32 1 0 0 0 0 21 28 1 6 0 0 0 21 36 1 0 0 0 0 22 33 2 0 0 0 0 22 37 1 0 0 0 0 23 25 1 0 0 0 0 23 29 1 6 0 0 0 24 34 2 0 0 0 0 24 36 1 0 0 0 0 25 37 1 0 0 0 0 26 27 1 1 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 28 35 1 0 0 0 0 29 30 1 1 0 0 0 30 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.29
Volume:	527.083
LogP:	3.541
LogD:	2.284
LogS:	-4.091
# Rotatable Bonds:	2
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.484
Synthetic Accessibility Score:	6.484
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.095
MDCK Permeability:	2.134391979780048e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.964
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.869
Plasma Protein Binding (PPB):	68.57798767089844%
Volume Distribution (VD):	1.114
Pgp-substrate:	20.981897354125977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.146
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.409
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.106
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.924
CYP3A4-substrate:	0.367

ADMET: Excretion

Clearance (CL):	5.737
Half-life (T1/2):	0.403

ADMET: Toxicity

hERG Blockers:	0.261
Human Hepatotoxicity (H-HT):	0.794
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.958
Carcinogencity:	0.762
Eye Corrosion:	0.008
Eye Irritation:	0.037
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC470076

Natural Product ID:	NPC470076
*Common Name:**	Angustifodilactone B
IUPAC Name:	n.a.
Synonyms:	Angustifodilactone B
Standard InCHIKey:	QCYCYOUXODNCMX-LDUYZNKBSA-N
Standard InCHI:	InChI=1S/C30H42O7/c1-16-7-8-21(36-24(16)34)28(6,35)18-9-11-26(4)19-13-17(31)23-25(2,3)37-22(33)10-12-29(23)15-30(19,29)14-20(32)27(18,26)5/h7,10,12,17-21,23,31-32,35H,8-9,11,13-15H2,1-6H3/t17-,18-,19-,20-,21+,23-,26-,27-,28+,29+,30-/m0/s1
SMILES:	O=C1C=C[C@]23[C@H](C(O1)(C)C)[C@@H](O)C[C@@H]1[C@@]3(C2)C[C@H](O)[C@]2([C@@]1(C)CC[C@@H]2[C@]([C@H]1CC=C(C(=O)O1)C)(O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669431
PubChem CID:	51003491
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
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	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	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		CC50	=	182.1	ug.mL-1	PMID[468073]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	13.6	ug.mL-1	PMID[468073]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	13.4	n.a.	PMID[468073]

☑ 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 NPC470076 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	212
0.1-0.2	1333
0.2-0.3	4182
0.3-0.4	8004
0.4-0.5	13244
0.5-0.6	6460
0.6-0.7	6428
0.7-0.8	2624
0.8-0.85	181
0.85-0.9	25
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9623	High Similarity	NPC470075
0.9314	High Similarity	NPC297617
0.8991	High Similarity	NPC216665
0.8818	High Similarity	NPC43213
0.875	High Similarity	NPC475617
0.8684	High Similarity	NPC67569
0.8673	High Similarity	NPC278681
0.8609	High Similarity	NPC470265
0.8609	High Similarity	NPC23786
0.8596	High Similarity	NPC112936
0.8585	High Similarity	NPC474124
0.8584	High Similarity	NPC16701
0.8545	High Similarity	NPC71680
0.8534	High Similarity	NPC469789
0.8532	High Similarity	NPC284828
0.8532	High Similarity	NPC5475
0.8532	High Similarity	NPC173905
0.8532	High Similarity	NPC472216
0.8509	High Similarity	NPC213761
0.8509	High Similarity	NPC35171
0.8505	High Similarity	NPC473543
0.8496	Intermediate Similarity	NPC157380
0.8496	Intermediate Similarity	NPC185287
0.8491	Intermediate Similarity	NPC475344
0.8491	Intermediate Similarity	NPC476471
0.8476	Intermediate Similarity	NPC473510
0.8476	Intermediate Similarity	NPC38855
0.8468	Intermediate Similarity	NPC470063
0.8462	Intermediate Similarity	NPC210337
0.8455	Intermediate Similarity	NPC15551
0.8426	Intermediate Similarity	NPC220217
0.8426	Intermediate Similarity	NPC119855
0.8421	Intermediate Similarity	NPC709
0.8421	Intermediate Similarity	NPC50774
0.8411	Intermediate Similarity	NPC472821
0.8411	Intermediate Similarity	NPC473523
0.8396	Intermediate Similarity	NPC11974
0.8393	Intermediate Similarity	NPC171126
0.839	Intermediate Similarity	NPC293112
0.8381	Intermediate Similarity	NPC218107
0.8378	Intermediate Similarity	NPC255401
0.8378	Intermediate Similarity	NPC284162
0.8378	Intermediate Similarity	NPC262083
0.8378	Intermediate Similarity	NPC471484
0.8376	Intermediate Similarity	NPC11895
0.8365	Intermediate Similarity	NPC88009
0.8333	Intermediate Similarity	NPC473656
0.8333	Intermediate Similarity	NPC140055
0.8333	Intermediate Similarity	NPC474550
0.8333	Intermediate Similarity	NPC473577
0.8333	Intermediate Similarity	NPC167606
0.8333	Intermediate Similarity	NPC475585
0.8333	Intermediate Similarity	NPC286528
0.8333	Intermediate Similarity	NPC20302
0.8318	Intermediate Similarity	NPC475038
0.8318	Intermediate Similarity	NPC109195
0.8318	Intermediate Similarity	NPC470972
0.8318	Intermediate Similarity	NPC472552
0.8305	Intermediate Similarity	NPC8369
0.8305	Intermediate Similarity	NPC8374
0.8304	Intermediate Similarity	NPC241477
0.8304	Intermediate Similarity	NPC44537
0.8304	Intermediate Similarity	NPC236217
0.8302	Intermediate Similarity	NPC230546
0.8291	Intermediate Similarity	NPC170538
0.8288	Intermediate Similarity	NPC181298
0.8288	Intermediate Similarity	NPC103491
0.8288	Intermediate Similarity	NPC472214
0.8288	Intermediate Similarity	NPC472215
0.8288	Intermediate Similarity	NPC238850
0.8276	Intermediate Similarity	NPC79579
0.8276	Intermediate Similarity	NPC474370
0.8273	Intermediate Similarity	NPC472218
0.8273	Intermediate Similarity	NPC472217
0.8273	Intermediate Similarity	NPC472219
0.8273	Intermediate Similarity	NPC475263
0.8273	Intermediate Similarity	NPC88701
0.8269	Intermediate Similarity	NPC276110
0.8269	Intermediate Similarity	NPC8774
0.8261	Intermediate Similarity	NPC153440
0.8261	Intermediate Similarity	NPC146280
0.8261	Intermediate Similarity	NPC124676
0.8257	Intermediate Similarity	NPC470980
0.8257	Intermediate Similarity	NPC88349
0.8257	Intermediate Similarity	NPC475290
0.8257	Intermediate Similarity	NPC186668
0.8246	Intermediate Similarity	NPC113425
0.8246	Intermediate Similarity	NPC207637
0.8246	Intermediate Similarity	NPC232564
0.8246	Intermediate Similarity	NPC190286
0.8241	Intermediate Similarity	NPC97487
0.8241	Intermediate Similarity	NPC10232
0.8241	Intermediate Similarity	NPC474822
0.8241	Intermediate Similarity	NPC196471
0.8241	Intermediate Similarity	NPC160583
0.8241	Intermediate Similarity	NPC23584
0.8241	Intermediate Similarity	NPC189588
0.8241	Intermediate Similarity	NPC187302
0.8235	Intermediate Similarity	NPC473635
0.8224	Intermediate Similarity	NPC247701
0.8224	Intermediate Similarity	NPC295110
0.8224	Intermediate Similarity	NPC268829
0.8224	Intermediate Similarity	NPC25177
0.8224	Intermediate Similarity	NPC472554
0.8224	Intermediate Similarity	NPC289670
0.8224	Intermediate Similarity	NPC222875
0.8208	Intermediate Similarity	NPC300179
0.8208	Intermediate Similarity	NPC470067
0.8208	Intermediate Similarity	NPC98868
0.8208	Intermediate Similarity	NPC102426
0.8208	Intermediate Similarity	NPC470066
0.8205	Intermediate Similarity	NPC312481
0.8205	Intermediate Similarity	NPC46570
0.8198	Intermediate Similarity	NPC75389
0.8198	Intermediate Similarity	NPC475274
0.819	Intermediate Similarity	NPC276103
0.819	Intermediate Similarity	NPC288970
0.819	Intermediate Similarity	NPC471903
0.819	Intermediate Similarity	NPC475041
0.819	Intermediate Similarity	NPC473636
0.819	Intermediate Similarity	NPC98457
0.819	Intermediate Similarity	NPC472667
0.819	Intermediate Similarity	NPC473839
0.819	Intermediate Similarity	NPC264954
0.819	Intermediate Similarity	NPC77689
0.819	Intermediate Similarity	NPC5292
0.819	Intermediate Similarity	NPC54248
0.819	Intermediate Similarity	NPC211093
0.819	Intermediate Similarity	NPC227583
0.819	Intermediate Similarity	NPC12103
0.8182	Intermediate Similarity	NPC187435
0.8182	Intermediate Similarity	NPC473586
0.8182	Intermediate Similarity	NPC67321
0.8182	Intermediate Similarity	NPC473593
0.8174	Intermediate Similarity	NPC470493
0.8174	Intermediate Similarity	NPC203862
0.8174	Intermediate Similarity	NPC470492
0.8174	Intermediate Similarity	NPC183580
0.8174	Intermediate Similarity	NPC134430
0.8174	Intermediate Similarity	NPC312824
0.8174	Intermediate Similarity	NPC475809
0.8174	Intermediate Similarity	NPC290693
0.8173	Intermediate Similarity	NPC127718
0.8173	Intermediate Similarity	NPC119562
0.8173	Intermediate Similarity	NPC105490
0.8173	Intermediate Similarity	NPC279410
0.8173	Intermediate Similarity	NPC65402
0.8173	Intermediate Similarity	NPC476186
0.8158	Intermediate Similarity	NPC147912
0.8158	Intermediate Similarity	NPC31354
0.8158	Intermediate Similarity	NPC69576
0.8158	Intermediate Similarity	NPC67259
0.8158	Intermediate Similarity	NPC471633
0.8158	Intermediate Similarity	NPC84949
0.8155	Intermediate Similarity	NPC234335
0.8151	Intermediate Similarity	NPC81736
0.8151	Intermediate Similarity	NPC172154
0.8148	Intermediate Similarity	NPC11956
0.8142	Intermediate Similarity	NPC152117
0.8142	Intermediate Similarity	NPC234042
0.8142	Intermediate Similarity	NPC277769
0.8142	Intermediate Similarity	NPC4573
0.8136	Intermediate Similarity	NPC88326
0.8136	Intermediate Similarity	NPC153700
0.8136	Intermediate Similarity	NPC107493
0.8131	Intermediate Similarity	NPC227865
0.8131	Intermediate Similarity	NPC251680
0.8125	Intermediate Similarity	NPC12795
0.8125	Intermediate Similarity	NPC177047
0.812	Intermediate Similarity	NPC135369
0.812	Intermediate Similarity	NPC475885
0.812	Intermediate Similarity	NPC474585
0.8113	Intermediate Similarity	NPC475032
0.8113	Intermediate Similarity	NPC475033
0.8113	Intermediate Similarity	NPC99726
0.8113	Intermediate Similarity	NPC205143
0.8108	Intermediate Similarity	NPC275060
0.8108	Intermediate Similarity	NPC181994
0.8108	Intermediate Similarity	NPC472825
0.8108	Intermediate Similarity	NPC38948
0.8108	Intermediate Similarity	NPC137462
0.8108	Intermediate Similarity	NPC304276
0.8103	Intermediate Similarity	NPC475372
0.8095	Intermediate Similarity	NPC281134
0.8087	Intermediate Similarity	NPC176840
0.8087	Intermediate Similarity	NPC471127
0.8087	Intermediate Similarity	NPC5311
0.8087	Intermediate Similarity	NPC234858
0.8087	Intermediate Similarity	NPC154363
0.8087	Intermediate Similarity	NPC310341
0.8087	Intermediate Similarity	NPC193382
0.8087	Intermediate Similarity	NPC99620
0.8087	Intermediate Similarity	NPC199428
0.8077	Intermediate Similarity	NPC53555
0.8077	Intermediate Similarity	NPC476304
0.8077	Intermediate Similarity	NPC7349
0.8073	Intermediate Similarity	NPC112009
0.8073	Intermediate Similarity	NPC475623
0.8073	Intermediate Similarity	NPC473694
0.8073	Intermediate Similarity	NPC475334

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 NPC470076 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1417
0.2-0.3	3790
0.3-0.4	2548
0.4-0.5	722
0.5-0.6	240
0.6-0.7	184
0.7-0.8	69
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7115	Discovery
0.8208	Intermediate Similarity	NPD7638	Approved
0.8131	Intermediate Similarity	NPD7640	Approved
0.8131	Intermediate Similarity	NPD7639	Approved
0.8051	Intermediate Similarity	NPD7503	Approved
0.7949	Intermediate Similarity	NPD7327	Approved
0.7949	Intermediate Similarity	NPD7328	Approved
0.7899	Intermediate Similarity	NPD8033	Approved
0.789	Intermediate Similarity	NPD5344	Discontinued
0.7881	Intermediate Similarity	NPD7516	Approved
0.787	Intermediate Similarity	NPD4225	Approved
0.7815	Intermediate Similarity	NPD8377	Approved
0.7815	Intermediate Similarity	NPD8294	Approved
0.775	Intermediate Similarity	NPD8378	Approved
0.775	Intermediate Similarity	NPD8335	Approved
0.775	Intermediate Similarity	NPD8296	Approved
0.775	Intermediate Similarity	NPD8380	Approved
0.775	Intermediate Similarity	NPD8379	Approved
0.7719	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7507	Approved
0.7632	Intermediate Similarity	NPD6686	Approved
0.7607	Intermediate Similarity	NPD4632	Approved
0.7521	Intermediate Similarity	NPD6319	Approved
0.7521	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD7632	Discontinued
0.748	Intermediate Similarity	NPD7604	Phase 2
0.7478	Intermediate Similarity	NPD6881	Approved
0.7478	Intermediate Similarity	NPD6899	Approved
0.7477	Intermediate Similarity	NPD6648	Approved
0.746	Intermediate Similarity	NPD7319	Approved
0.7391	Intermediate Similarity	NPD5697	Approved
0.7383	Intermediate Similarity	NPD7838	Discovery
0.7373	Intermediate Similarity	NPD6053	Discontinued
0.735	Intermediate Similarity	NPD7290	Approved
0.735	Intermediate Similarity	NPD6883	Approved
0.735	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7102	Approved
0.735	Intermediate Similarity	NPD6371	Approved
0.7304	Intermediate Similarity	NPD7128	Approved
0.7304	Intermediate Similarity	NPD5739	Approved
0.7304	Intermediate Similarity	NPD6675	Approved
0.7304	Intermediate Similarity	NPD6402	Approved
0.7288	Intermediate Similarity	NPD6869	Approved
0.7288	Intermediate Similarity	NPD6650	Approved
0.7288	Intermediate Similarity	NPD6649	Approved
0.7288	Intermediate Similarity	NPD6617	Approved
0.7288	Intermediate Similarity	NPD8130	Phase 1
0.7288	Intermediate Similarity	NPD6847	Approved
0.728	Intermediate Similarity	NPD7492	Approved
0.7273	Intermediate Similarity	NPD6009	Approved
0.7265	Intermediate Similarity	NPD6014	Approved
0.7265	Intermediate Similarity	NPD6012	Approved
0.7265	Intermediate Similarity	NPD6013	Approved
0.7236	Intermediate Similarity	NPD6054	Approved
0.7227	Intermediate Similarity	NPD6882	Approved
0.7222	Intermediate Similarity	NPD6616	Approved
0.7179	Intermediate Similarity	NPD7320	Approved
0.7179	Intermediate Similarity	NPD6011	Approved
0.7177	Intermediate Similarity	NPD5983	Phase 2
0.7165	Intermediate Similarity	NPD7078	Approved
0.7156	Intermediate Similarity	NPD7637	Suspended
0.7155	Intermediate Similarity	NPD6008	Approved
0.712	Intermediate Similarity	NPD6370	Approved
0.7119	Intermediate Similarity	NPD6373	Approved
0.7119	Intermediate Similarity	NPD6372	Approved
0.7109	Intermediate Similarity	NPD7736	Approved
0.7103	Intermediate Similarity	NPD7524	Approved
0.7094	Intermediate Similarity	NPD6412	Phase 2
0.7094	Intermediate Similarity	NPD5701	Approved
0.7094	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6399	Phase 3
0.7087	Intermediate Similarity	NPD7525	Registered
0.7087	Intermediate Similarity	NPD6336	Discontinued
0.7064	Intermediate Similarity	NPD46	Approved
0.7064	Intermediate Similarity	NPD6698	Approved
0.7059	Intermediate Similarity	NPD4634	Approved
0.7043	Intermediate Similarity	NPD5211	Phase 2
0.704	Intermediate Similarity	NPD6015	Approved
0.704	Intermediate Similarity	NPD6016	Approved
0.7034	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD8133	Approved
0.7018	Intermediate Similarity	NPD5286	Approved
0.7018	Intermediate Similarity	NPD5285	Approved
0.7018	Intermediate Similarity	NPD4696	Approved
0.7	Intermediate Similarity	NPD6079	Approved
0.6991	Remote Similarity	NPD6083	Phase 2
0.6991	Remote Similarity	NPD6084	Phase 2
0.6984	Remote Similarity	NPD5988	Approved
0.6981	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6051	Approved
0.696	Remote Similarity	NPD6059	Approved
0.6923	Remote Similarity	NPD5141	Approved
0.6899	Remote Similarity	NPD8293	Discontinued
0.6897	Remote Similarity	NPD4633	Approved
0.6897	Remote Similarity	NPD5226	Approved
0.6897	Remote Similarity	NPD5225	Approved
0.6897	Remote Similarity	NPD5224	Approved
0.6887	Remote Similarity	NPD6695	Phase 3
0.688	Remote Similarity	NPD7101	Approved
0.688	Remote Similarity	NPD7100	Approved
0.686	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4755	Approved
0.6838	Remote Similarity	NPD5174	Approved
0.6838	Remote Similarity	NPD5175	Approved
0.6818	Remote Similarity	NPD5328	Approved
0.6814	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5223	Approved
0.6807	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6335	Approved
0.6786	Remote Similarity	NPD4202	Approved
0.6783	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6274	Approved
0.6754	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5222	Approved
0.6754	Remote Similarity	NPD5221	Approved
0.6726	Remote Similarity	NPD7748	Approved
0.6724	Remote Similarity	NPD4700	Approved
0.672	Remote Similarity	NPD6317	Approved
0.6698	Remote Similarity	NPD6902	Approved
0.6697	Remote Similarity	NPD3618	Phase 1
0.6696	Remote Similarity	NPD7515	Phase 2
0.6696	Remote Similarity	NPD8035	Phase 2
0.6696	Remote Similarity	NPD8034	Phase 2
0.6696	Remote Similarity	NPD5173	Approved
0.6696	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6641	Remote Similarity	NPD8513	Phase 3
0.664	Remote Similarity	NPD6868	Approved
0.6638	Remote Similarity	NPD5696	Approved
0.6636	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7750	Discontinued
0.6612	Remote Similarity	NPD4730	Approved
0.6612	Remote Similarity	NPD4729	Approved
0.6606	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6931	Approved
0.6604	Remote Similarity	NPD6930	Phase 2
0.6604	Remote Similarity	NPD7514	Phase 3
0.6602	Remote Similarity	NPD7339	Approved
0.6602	Remote Similarity	NPD6942	Approved
0.6585	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6672	Approved
0.6577	Remote Similarity	NPD5737	Approved
0.6567	Remote Similarity	NPD7260	Phase 2
0.6557	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5693	Phase 1
0.6545	Remote Similarity	NPD7334	Approved
0.6545	Remote Similarity	NPD6409	Approved
0.6545	Remote Similarity	NPD7521	Approved
0.6545	Remote Similarity	NPD6684	Approved
0.6545	Remote Similarity	NPD5330	Approved
0.6545	Remote Similarity	NPD7146	Approved
0.6538	Remote Similarity	NPD8328	Phase 3
0.6538	Remote Similarity	NPD6933	Approved
0.6522	Remote Similarity	NPD4629	Approved
0.6522	Remote Similarity	NPD5210	Approved
0.6518	Remote Similarity	NPD4753	Phase 2
0.6514	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6908	Approved
0.6512	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8516	Approved
0.6512	Remote Similarity	NPD6909	Approved
0.6512	Remote Similarity	NPD8515	Approved
0.6512	Remote Similarity	NPD8517	Approved
0.6509	Remote Similarity	NPD4195	Approved
0.6509	Remote Similarity	NPD6929	Approved
0.6504	Remote Similarity	NPD5249	Phase 3
0.6504	Remote Similarity	NPD5248	Approved
0.6504	Remote Similarity	NPD5250	Approved
0.6504	Remote Similarity	NPD5251	Approved
0.6504	Remote Similarity	NPD5247	Approved
0.6481	Remote Similarity	NPD3667	Approved
0.6476	Remote Similarity	NPD6932	Approved
0.6475	Remote Similarity	NPD5128	Approved
0.6466	Remote Similarity	NPD6033	Approved
0.6466	Remote Similarity	NPD4697	Phase 3
0.646	Remote Similarity	NPD5785	Approved
0.6455	Remote Similarity	NPD1694	Approved
0.6452	Remote Similarity	NPD5217	Approved
0.6452	Remote Similarity	NPD5216	Approved
0.6452	Remote Similarity	NPD5215	Approved
0.6449	Remote Similarity	NPD7332	Phase 2
0.6446	Remote Similarity	NPD4768	Approved
0.6446	Remote Similarity	NPD4767	Approved
0.6435	Remote Similarity	NPD7900	Approved
0.6435	Remote Similarity	NPD6001	Approved
0.6435	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6903	Approved
0.6417	Remote Similarity	NPD4754	Approved
0.6415	Remote Similarity	NPD7145	Approved
0.6412	Remote Similarity	NPD6067	Discontinued
0.6404	Remote Similarity	NPD5284	Approved
0.6404	Remote Similarity	NPD7087	Discontinued
0.6404	Remote Similarity	NPD5281	Approved
0.6389	Remote Similarity	NPD7625	Phase 1

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