NPASS Compound

Structure

CID94529 OpenBabel06191715432D 38 42 0 0 1 0 0 0 0 0999 V2000 0.7184 -2.9331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1846 -3.7791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2158 -4.0074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2467 1.4673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7413 0.5918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6715 1.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 0.4897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -0.9780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8479 1.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -1.9560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5417 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3889 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5423 2.4451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8481 -2.4454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6957 -2.9329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2854 -3.7049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6953 0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6955 -1.9556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5418 -0.4893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5415 -0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3891 2.9340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3891 0.9784 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6950 -0.0004 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8476 -0.4885 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2359 2.4451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2359 1.4673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5423 1.4673 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8474 -0.4889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8479 -1.4671 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4417 -4.3594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -1.4893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2484 0.2192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3891 3.9448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1113 2.9505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0823 -2.7479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 19 2 0 0 0 0 10 31 1 0 0 0 0 11 12 1 0 0 0 0 11 30 1 0 0 0 0 12 32 1 0 0 0 0 13 20 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 24 1 0 0 0 0 15 23 1 0 0 0 0 15 29 1 0 0 0 0 16 38 1 0 0 0 0 17 20 1 0 0 0 0 18 33 2 0 0 0 0 18 38 1 0 0 0 0 19 25 1 0 0 0 0 19 29 1 0 0 0 0 20 32 1 1 0 0 0 21 25 1 0 0 0 0 21 34 1 1 0 0 0 22 26 1 0 0 0 0 22 35 1 6 0 0 0 23 27 1 0 0 0 0 23 36 1 6 0 0 0 24 28 1 0 0 0 0 24 29 1 1 0 0 0 25 30 1 6 0 0 0 26 31 1 1 0 0 0 26 32 1 0 0 0 0 27 28 1 0 0 0 0 27 37 2 0 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 8 1 1 0 0 0 32 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.36
Volume:	564.078
LogP:	4.285
LogD:	3.957
LogS:	-4.354
# Rotatable Bonds:	4
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.361
Synthetic Accessibility Score:	5.489
Fsp3:	0.875
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:	-5.171
MDCK Permeability:	9.361407137475908e-06
Pgp-inhibitor:	0.888
Pgp-substrate:	0.319
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.677
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.698
Plasma Protein Binding (PPB):	68.07574462890625%
Volume Distribution (VD):	0.741
Pgp-substrate:	19.890361785888672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.838
CYP2C9-inhibitor:	0.102
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.758
CYP3A4-substrate:	0.444

ADMET: Excretion

Clearance (CL):	4.891
Half-life (T1/2):	0.186

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.837
Maximum Recommended Daily Dose:	0.715
Skin Sensitization:	0.224
Carcinogencity:	0.12
Eye Corrosion:	0.084
Eye Irritation:	0.028
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: NPC94529

Natural Product ID:	NPC94529
*Common Name:**	Rubianol-B
IUPAC Name:	[(1R,3S,3aR,5aS,5bS,6S,7aR,10R,11aS,13aR,13bR)-1,6,10-trihydroxy-5a,8,8,11a,13a-pentamethyl-9-oxo-3-propan-2-yl-2,3,4,5,5b,6,7,7a,10,11,13,13b-dodecahydro-1H-cyclopenta[a]chrysen-3a-yl]methyl acetate
Synonyms:	Rubianol-B
Standard InCHIKey:	IWIVDUNOLOIWLV-MHQBMSPJSA-N
Standard InCHI:	InChI=1S/C32H50O6/c1-17(2)20-13-22(35)26-31(8)10-9-19-25(30(31,7)11-12-32(20,26)16-38-18(3)33)21(34)14-24-28(4,5)27(37)23(36)15-29(19,24)6/h9,17,20-26,34-36H,10-16H2,1-8H3/t20-,21-,22+,23+,24-,25-,26+,29+,30-,31+,32+/m0/s1
SMILES:	CC(=O)OC[C@]12CC[C@@]3([C@]([C@H]2[C@@H](C[C@H]1C(C)C)O)(C)CC=C1[C@H]3[C@@H](O)C[C@@H]2[C@]1(C)C[C@H](C(=O)C2(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460714
PubChem CID:	21629622
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
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350148]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762798]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21044847]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	root	n.a.	PMID[21973054]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[21973054]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	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	5

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	-5.8	%	PMID[448654]
NPT2	Others	Unspecified	Inhibition	=	0.0	%	PMID[448654]
NPT2	Others	Unspecified	Inhibition	=	-1.5	%	PMID[448654]
NPT2	Others	Unspecified	Inhibition	=	-1.1	%	PMID[448654]
NPT2	Others	Unspecified	Inhibition	=	15.4	%	PMID[448654]

☑ 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 NPC94529 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	216
0.1-0.2	1404
0.2-0.3	4702
0.3-0.4	10123
0.4-0.5	11191
0.5-0.6	5840
0.6-0.7	4820
0.7-0.8	3943
0.8-0.85	379
0.85-0.9	67
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9798	High Similarity	NPC278628
0.9798	High Similarity	NPC231530
0.9406	High Similarity	NPC475571
0.9307	High Similarity	NPC29705
0.9293	High Similarity	NPC15390
0.9231	High Similarity	NPC197428
0.9151	High Similarity	NPC202889
0.9091	High Similarity	NPC190554
0.9057	High Similarity	NPC71348
0.9057	High Similarity	NPC280782
0.9029	High Similarity	NPC196528
0.902	High Similarity	NPC140723
0.899	High Similarity	NPC304899
0.899	High Similarity	NPC253115
0.8981	High Similarity	NPC270958
0.8818	High Similarity	NPC118638
0.8812	High Similarity	NPC477854
0.8812	High Similarity	NPC260149
0.8812	High Similarity	NPC58942
0.88	High Similarity	NPC42042
0.88	High Similarity	NPC173272
0.8796	High Similarity	NPC194100
0.8785	High Similarity	NPC118860
0.8785	High Similarity	NPC214797
0.8785	High Similarity	NPC231589
0.8774	High Similarity	NPC241927
0.8774	High Similarity	NPC258543
0.8738	High Similarity	NPC22388
0.8725	High Similarity	NPC218383
0.8725	High Similarity	NPC83709
0.8725	High Similarity	NPC208358
0.8704	High Similarity	NPC170487
0.87	High Similarity	NPC279974
0.87	High Similarity	NPC48330
0.87	High Similarity	NPC469599
0.8679	High Similarity	NPC211224
0.8667	High Similarity	NPC181265
0.8654	High Similarity	NPC469985
0.8641	High Similarity	NPC155974
0.8627	High Similarity	NPC119036
0.8624	High Similarity	NPC52634
0.8614	High Similarity	NPC477853
0.8611	High Similarity	NPC470281
0.8585	High Similarity	NPC44063
0.8571	High Similarity	NPC96268
0.8571	High Similarity	NPC235889
0.8571	High Similarity	NPC310586
0.8571	High Similarity	NPC47281
0.8558	High Similarity	NPC477054
0.8558	High Similarity	NPC15396
0.8519	High Similarity	NPC163314
0.8515	High Similarity	NPC69548
0.8515	High Similarity	NPC184848
0.8515	High Similarity	NPC473240
0.8515	High Similarity	NPC474727
0.8509	High Similarity	NPC65858
0.85	High Similarity	NPC206810
0.85	High Similarity	NPC470376
0.85	High Similarity	NPC470375
0.85	High Similarity	NPC473678
0.8496	Intermediate Similarity	NPC471406
0.8491	Intermediate Similarity	NPC50535
0.8491	Intermediate Similarity	NPC265127
0.8491	Intermediate Similarity	NPC28791
0.8485	Intermediate Similarity	NPC471896
0.8476	Intermediate Similarity	NPC191892
0.8476	Intermediate Similarity	NPC159442
0.8476	Intermediate Similarity	NPC275583
0.8462	Intermediate Similarity	NPC474327
0.8462	Intermediate Similarity	NPC477053
0.8462	Intermediate Similarity	NPC477052
0.8462	Intermediate Similarity	NPC121218
0.8462	Intermediate Similarity	NPC477051
0.8462	Intermediate Similarity	NPC253886
0.8455	Intermediate Similarity	NPC472926
0.8455	Intermediate Similarity	NPC962
0.8447	Intermediate Similarity	NPC114274
0.8447	Intermediate Similarity	NPC477813
0.8447	Intermediate Similarity	NPC475876
0.844	Intermediate Similarity	NPC43775
0.8435	Intermediate Similarity	NPC43252
0.8435	Intermediate Similarity	NPC135038
0.8431	Intermediate Similarity	NPC96859
0.8431	Intermediate Similarity	NPC328162
0.8431	Intermediate Similarity	NPC200054
0.8431	Intermediate Similarity	NPC476318
0.8431	Intermediate Similarity	NPC29410
0.8431	Intermediate Similarity	NPC476327
0.8431	Intermediate Similarity	NPC305483
0.8431	Intermediate Similarity	NPC49371
0.8426	Intermediate Similarity	NPC304495
0.8426	Intermediate Similarity	NPC2766
0.8416	Intermediate Similarity	NPC245972
0.8416	Intermediate Similarity	NPC111015
0.8416	Intermediate Similarity	NPC196485
0.8411	Intermediate Similarity	NPC59530
0.8411	Intermediate Similarity	NPC144854
0.8411	Intermediate Similarity	NPC3316
0.8411	Intermediate Similarity	NPC251824
0.8411	Intermediate Similarity	NPC86852
0.8407	Intermediate Similarity	NPC475041
0.84	Intermediate Similarity	NPC154101
0.84	Intermediate Similarity	NPC26888
0.8396	Intermediate Similarity	NPC477812
0.8396	Intermediate Similarity	NPC137657
0.8381	Intermediate Similarity	NPC136289
0.8381	Intermediate Similarity	NPC473928
0.8381	Intermediate Similarity	NPC193934
0.8381	Intermediate Similarity	NPC271980
0.8381	Intermediate Similarity	NPC170615
0.8365	Intermediate Similarity	NPC167974
0.8365	Intermediate Similarity	NPC472972
0.835	Intermediate Similarity	NPC18509
0.835	Intermediate Similarity	NPC476879
0.835	Intermediate Similarity	NPC475033
0.835	Intermediate Similarity	NPC476878
0.835	Intermediate Similarity	NPC189880
0.835	Intermediate Similarity	NPC108078
0.835	Intermediate Similarity	NPC475032
0.8348	Intermediate Similarity	NPC222688
0.8333	Intermediate Similarity	NPC154608
0.8333	Intermediate Similarity	NPC109973
0.8333	Intermediate Similarity	NPC192813
0.8333	Intermediate Similarity	NPC317586
0.8333	Intermediate Similarity	NPC277017
0.8333	Intermediate Similarity	NPC469845
0.8333	Intermediate Similarity	NPC472219
0.8333	Intermediate Similarity	NPC293850
0.8333	Intermediate Similarity	NPC472217
0.8333	Intermediate Similarity	NPC470269
0.8333	Intermediate Similarity	NPC275539
0.8333	Intermediate Similarity	NPC189075
0.8333	Intermediate Similarity	NPC98639
0.8333	Intermediate Similarity	NPC472218
0.8333	Intermediate Similarity	NPC470016
0.8319	Intermediate Similarity	NPC324253
0.8318	Intermediate Similarity	NPC37600
0.8317	Intermediate Similarity	NPC244356
0.8317	Intermediate Similarity	NPC224060
0.8317	Intermediate Similarity	NPC109414
0.8317	Intermediate Similarity	NPC477855
0.8304	Intermediate Similarity	NPC49492
0.8304	Intermediate Similarity	NPC148458
0.8304	Intermediate Similarity	NPC266728
0.8302	Intermediate Similarity	NPC95585
0.8302	Intermediate Similarity	NPC282233
0.8302	Intermediate Similarity	NPC222153
0.8302	Intermediate Similarity	NPC87927
0.83	Intermediate Similarity	NPC148414
0.83	Intermediate Similarity	NPC175628
0.83	Intermediate Similarity	NPC111585
0.8288	Intermediate Similarity	NPC250109
0.8286	Intermediate Similarity	NPC289148
0.8286	Intermediate Similarity	NPC118964
0.8286	Intermediate Similarity	NPC52899
0.8286	Intermediate Similarity	NPC81530
0.8286	Intermediate Similarity	NPC163963
0.8276	Intermediate Similarity	NPC267822
0.8273	Intermediate Similarity	NPC201992
0.8269	Intermediate Similarity	NPC38296
0.8269	Intermediate Similarity	NPC153792
0.8269	Intermediate Similarity	NPC20479
0.8269	Intermediate Similarity	NPC162459
0.8269	Intermediate Similarity	NPC38471
0.8269	Intermediate Similarity	NPC98837
0.8269	Intermediate Similarity	NPC471038
0.8269	Intermediate Similarity	NPC28864
0.8269	Intermediate Similarity	NPC271387
0.8261	Intermediate Similarity	NPC470921
0.8257	Intermediate Similarity	NPC141350
0.8252	Intermediate Similarity	NPC475178
0.8252	Intermediate Similarity	NPC157113
0.8252	Intermediate Similarity	NPC329910
0.8252	Intermediate Similarity	NPC219353
0.8252	Intermediate Similarity	NPC62516
0.8252	Intermediate Similarity	NPC327179
0.8241	Intermediate Similarity	NPC475294
0.8241	Intermediate Similarity	NPC165873
0.8241	Intermediate Similarity	NPC220974
0.8241	Intermediate Similarity	NPC472925
0.8241	Intermediate Similarity	NPC110496
0.8235	Intermediate Similarity	NPC166906
0.8235	Intermediate Similarity	NPC159410
0.823	Intermediate Similarity	NPC239273
0.823	Intermediate Similarity	NPC472927
0.823	Intermediate Similarity	NPC471854
0.8224	Intermediate Similarity	NPC475036
0.8224	Intermediate Similarity	NPC149124
0.8224	Intermediate Similarity	NPC28656
0.8224	Intermediate Similarity	NPC75531
0.8224	Intermediate Similarity	NPC471293
0.8218	Intermediate Similarity	NPC23434
0.8218	Intermediate Similarity	NPC60755
0.8218	Intermediate Similarity	NPC185936
0.8218	Intermediate Similarity	NPC474525
0.8218	Intermediate Similarity	NPC470590
0.8218	Intermediate Similarity	NPC168027
0.8218	Intermediate Similarity	NPC77099
0.8218	Intermediate Similarity	NPC285184
0.8214	Intermediate Similarity	NPC474906

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 NPC94529 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1626
0.2-0.3	3922
0.3-0.4	2239
0.4-0.5	656
0.5-0.6	190
0.6-0.7	144
0.7-0.8	136
0.8-0.85	43
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8846	High Similarity	NPD5739	Approved
0.8846	High Similarity	NPD6402	Approved
0.8846	High Similarity	NPD7128	Approved
0.8846	High Similarity	NPD6675	Approved
0.8679	High Similarity	NPD7320	Approved
0.8679	High Similarity	NPD6899	Approved
0.8679	High Similarity	NPD6881	Approved
0.8611	High Similarity	NPD8130	Phase 1
0.8598	High Similarity	NPD6372	Approved
0.8598	High Similarity	NPD6373	Approved
0.8585	High Similarity	NPD5701	Approved
0.8585	High Similarity	NPD5697	Approved
0.8532	High Similarity	NPD8297	Approved
0.8519	High Similarity	NPD7290	Approved
0.8519	High Similarity	NPD7102	Approved
0.8519	High Similarity	NPD6883	Approved
0.8505	High Similarity	NPD6011	Approved
0.8455	Intermediate Similarity	NPD4632	Approved
0.844	Intermediate Similarity	NPD6617	Approved
0.844	Intermediate Similarity	NPD6847	Approved
0.844	Intermediate Similarity	NPD6649	Approved
0.844	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD6869	Approved
0.844	Intermediate Similarity	NPD6650	Approved
0.8426	Intermediate Similarity	NPD6012	Approved
0.8426	Intermediate Similarity	NPD6013	Approved
0.8426	Intermediate Similarity	NPD6014	Approved
0.8364	Intermediate Similarity	NPD6882	Approved
0.835	Intermediate Similarity	NPD4755	Approved
0.8318	Intermediate Similarity	NPD6008	Approved
0.8317	Intermediate Similarity	NPD6399	Phase 3
0.8305	Intermediate Similarity	NPD7736	Approved
0.823	Intermediate Similarity	NPD6009	Approved
0.819	Intermediate Similarity	NPD5285	Approved
0.819	Intermediate Similarity	NPD4696	Approved
0.819	Intermediate Similarity	NPD5286	Approved
0.819	Intermediate Similarity	NPD4700	Approved
0.8174	Intermediate Similarity	NPD6319	Approved
0.8173	Intermediate Similarity	NPD6083	Phase 2
0.8173	Intermediate Similarity	NPD6084	Phase 2
0.812	Intermediate Similarity	NPD7604	Phase 2
0.8113	Intermediate Similarity	NPD5223	Approved
0.8103	Intermediate Similarity	NPD5983	Phase 2
0.8095	Intermediate Similarity	NPD7638	Approved
0.8067	Intermediate Similarity	NPD8293	Discontinued
0.8058	Intermediate Similarity	NPD7748	Approved
0.8051	Intermediate Similarity	NPD7492	Approved
0.8039	Intermediate Similarity	NPD8034	Phase 2
0.8039	Intermediate Similarity	NPD8035	Phase 2
0.8037	Intermediate Similarity	NPD5211	Phase 2
0.8037	Intermediate Similarity	NPD5226	Approved
0.8037	Intermediate Similarity	NPD5224	Approved
0.8037	Intermediate Similarity	NPD5225	Approved
0.8037	Intermediate Similarity	NPD4633	Approved
0.802	Intermediate Similarity	NPD5328	Approved
0.8019	Intermediate Similarity	NPD7639	Approved
0.8019	Intermediate Similarity	NPD7640	Approved
0.8017	Intermediate Similarity	NPD6054	Approved
0.8017	Intermediate Similarity	NPD6059	Approved
0.8	Intermediate Similarity	NPD7902	Approved
0.8	Intermediate Similarity	NPD6335	Approved
0.7983	Intermediate Similarity	NPD6336	Discontinued
0.7983	Intermediate Similarity	NPD6616	Approved
0.7982	Intermediate Similarity	NPD6274	Approved
0.7963	Intermediate Similarity	NPD5175	Approved
0.7963	Intermediate Similarity	NPD4754	Approved
0.7963	Intermediate Similarity	NPD5174	Approved
0.7931	Intermediate Similarity	NPD7100	Approved
0.7931	Intermediate Similarity	NPD7101	Approved
0.7921	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7078	Approved
0.7913	Intermediate Similarity	NPD6317	Approved
0.7905	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5222	Approved
0.7905	Intermediate Similarity	NPD4697	Phase 3
0.7905	Intermediate Similarity	NPD5221	Approved
0.789	Intermediate Similarity	NPD5141	Approved
0.7881	Intermediate Similarity	NPD6370	Approved
0.7879	Intermediate Similarity	NPD4786	Approved
0.7864	Intermediate Similarity	NPD7515	Phase 2
0.7864	Intermediate Similarity	NPD6079	Approved
0.7857	Intermediate Similarity	NPD4634	Approved
0.7845	Intermediate Similarity	NPD6313	Approved
0.7845	Intermediate Similarity	NPD6314	Approved
0.783	Intermediate Similarity	NPD5173	Approved
0.7818	Intermediate Similarity	NPD4767	Approved
0.7818	Intermediate Similarity	NPD4768	Approved
0.781	Intermediate Similarity	NPD5695	Phase 3
0.78	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD6908	Approved
0.7797	Intermediate Similarity	NPD6015	Approved
0.7797	Intermediate Similarity	NPD6909	Approved
0.7797	Intermediate Similarity	NPD6016	Approved
0.7788	Intermediate Similarity	NPD4202	Approved
0.7757	Intermediate Similarity	NPD5696	Approved
0.7748	Intermediate Similarity	NPD6412	Phase 2
0.7745	Intermediate Similarity	NPD6672	Approved
0.7745	Intermediate Similarity	NPD5737	Approved
0.7731	Intermediate Similarity	NPD5988	Approved
0.7723	Intermediate Similarity	NPD5330	Approved
0.7723	Intermediate Similarity	NPD7146	Approved
0.7723	Intermediate Similarity	NPD6098	Approved
0.7723	Intermediate Similarity	NPD7334	Approved
0.7723	Intermediate Similarity	NPD6684	Approved
0.7723	Intermediate Similarity	NPD6409	Approved
0.7723	Intermediate Similarity	NPD7521	Approved
0.7714	Intermediate Similarity	NPD7900	Approved
0.7714	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD7507	Approved
0.7679	Intermediate Similarity	NPD4729	Approved
0.7679	Intermediate Similarity	NPD4730	Approved
0.7679	Intermediate Similarity	NPD5128	Approved
0.7677	Intermediate Similarity	NPD3667	Approved
0.7672	Intermediate Similarity	NPD6868	Approved
0.767	Intermediate Similarity	NPD6080	Approved
0.767	Intermediate Similarity	NPD6673	Approved
0.767	Intermediate Similarity	NPD4753	Phase 2
0.767	Intermediate Similarity	NPD6904	Approved
0.7667	Intermediate Similarity	NPD8328	Phase 3
0.7647	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD6903	Approved
0.7561	Intermediate Similarity	NPD6033	Approved
0.7549	Intermediate Similarity	NPD3618	Phase 1
0.7544	Intermediate Similarity	NPD5169	Approved
0.7544	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5250	Approved
0.7544	Intermediate Similarity	NPD5248	Approved
0.7544	Intermediate Similarity	NPD5251	Approved
0.7544	Intermediate Similarity	NPD5247	Approved
0.7544	Intermediate Similarity	NPD5135	Approved
0.7544	Intermediate Similarity	NPD5249	Phase 3
0.7525	Intermediate Similarity	NPD3666	Approved
0.7525	Intermediate Similarity	NPD3665	Phase 1
0.7525	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD7319	Approved
0.7478	Intermediate Similarity	NPD5217	Approved
0.7478	Intermediate Similarity	NPD5216	Approved
0.7478	Intermediate Similarity	NPD5215	Approved
0.7478	Intermediate Similarity	NPD5127	Approved
0.7477	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5329	Approved
0.7414	Intermediate Similarity	NPD6053	Discontinued
0.7387	Intermediate Similarity	NPD7632	Discontinued
0.7358	Intermediate Similarity	NPD5693	Phase 1
0.7358	Intermediate Similarity	NPD6050	Approved
0.7353	Intermediate Similarity	NPD4197	Approved
0.7315	Intermediate Similarity	NPD4629	Approved
0.7315	Intermediate Similarity	NPD5210	Approved
0.7311	Intermediate Similarity	NPD7115	Discovery
0.7304	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7525	Registered
0.7288	Intermediate Similarity	NPD5167	Approved
0.7273	Intermediate Similarity	NPD6114	Approved
0.7273	Intermediate Similarity	NPD6115	Approved
0.7273	Intermediate Similarity	NPD6697	Approved
0.7273	Intermediate Similarity	NPD6118	Approved
0.7264	Intermediate Similarity	NPD5692	Phase 3
0.7217	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5168	Approved
0.7213	Intermediate Similarity	NPD8033	Approved
0.7212	Intermediate Similarity	NPD5279	Phase 3
0.7203	Intermediate Similarity	NPD8133	Approved
0.7196	Intermediate Similarity	NPD6411	Approved
0.7196	Intermediate Similarity	NPD5281	Approved
0.7196	Intermediate Similarity	NPD5694	Approved
0.7196	Intermediate Similarity	NPD5284	Approved
0.7184	Intermediate Similarity	NPD3668	Phase 3
0.7176	Intermediate Similarity	NPD6334	Approved
0.7176	Intermediate Similarity	NPD6333	Approved
0.7172	Intermediate Similarity	NPD6116	Phase 1
0.717	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6435	Approved
0.7157	Intermediate Similarity	NPD4223	Phase 3
0.7157	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD3573	Approved
0.7131	Intermediate Similarity	NPD8377	Approved
0.7131	Intermediate Similarity	NPD8294	Approved
0.7107	Intermediate Similarity	NPD7327	Approved
0.7107	Intermediate Similarity	NPD7328	Approved
0.7097	Intermediate Similarity	NPD6067	Discontinued
0.7087	Intermediate Similarity	NPD4788	Approved
0.7075	Intermediate Similarity	NPD5208	Approved
0.7073	Intermediate Similarity	NPD8378	Approved
0.7073	Intermediate Similarity	NPD8379	Approved
0.7073	Intermediate Similarity	NPD8296	Approved
0.7073	Intermediate Similarity	NPD8380	Approved
0.7073	Intermediate Similarity	NPD8335	Approved
0.7071	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6117	Approved
0.7064	Intermediate Similarity	NPD6001	Approved
0.7049	Intermediate Similarity	NPD7516	Approved
0.7048	Intermediate Similarity	NPD5280	Approved
0.7048	Intermediate Similarity	NPD5690	Phase 2
0.7048	Intermediate Similarity	NPD4694	Approved
0.7009	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6101	Approved
0.6972	Remote Similarity	NPD5779	Approved
0.6972	Remote Similarity	NPD5778	Approved
0.697	Remote Similarity	NPD3703	Phase 2

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