NPASS Compound

Natural Product: NPC491935

Natural Product ID	NPC491935
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	triacontyl hexadec-7-enoate
IUPAC Name	triacontyl hexadec-7-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 138137 0 0 0 0 0 0 0 0999 V2000 -15.4236 4.0602 -0.1886 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.0946 3.5542 1.2070 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5038 2.0799 1.2742 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7459 1.2669 0.2439 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.2042 -0.1658 0.3700 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.4350 -0.9672 -0.6643 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.8864 -2.3831 -0.5560 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.2037 -3.3325 -1.4863 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7831 -3.5084 -1.1627 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2223 -2.9710 -0.0974 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7545 -3.2223 0.1183 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9596 -1.9332 0.1530 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5178 -2.3193 0.3475 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5675 -1.1764 0.4078 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7811 -0.2082 1.5218 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7119 0.8508 1.3539 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4371 1.6340 2.2933 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0246 0.9788 0.1785 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0250 1.8919 -0.1181 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8308 1.6724 0.7955 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3748 0.2659 0.5743 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1305 -0.1093 1.3675 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 0.7635 0.9791 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2802 0.4077 1.7232 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6213 -1.0069 1.4266 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8550 -1.5808 1.9626 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1974 -1.0812 1.6360 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6260 -1.0663 0.2054 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9870 -0.0862 -0.6972 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3482 1.3486 -0.3392 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8339 1.6178 -0.5261 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 1.4333 -1.9559 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7537 1.7161 -2.0295 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2697 1.6069 -3.4069 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1432 0.3814 -4.1692 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7970 -0.8953 -3.9718 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8419 -1.7328 -2.8096 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5433 -1.5529 -1.5477 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0292 -1.5281 -1.5225 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7774 -0.4313 -2.1621 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5818 0.9302 -1.5238 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0769 0.9347 -0.0851 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5384 0.6077 0.0003 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9463 0.6338 1.4659 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4269 0.3109 1.6041 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8611 0.3248 3.0335 C 0 0 0 0 0 0 0 0 0 0 0 0 16.3373 0.0058 3.1794 C 0 0 0 0 0 0 0 0 0 0 0 0 17.1979 1.0015 2.4466 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.2598 3.4584 -0.6174 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.5425 3.9563 -0.8295 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.7624 5.0964 -0.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.0161 3.6086 1.3931 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.7186 4.0751 1.9607 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.5805 2.0229 1.1017 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.2832 1.7308 2.2951 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.6637 1.2945 0.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9045 1.6458 -0.7698 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.2993 -0.2496 0.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9218 -0.5483 1.3804 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3942 -0.7297 -0.6353 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.8016 -0.5799 -1.6824 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.0010 -2.4760 -0.7262 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.7770 -2.6906 0.5199 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2233 -2.9096 -2.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.7235 -4.3334 -1.5045 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1420 -4.1263 -1.8473 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7853 -2.4010 0.6194 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3789 -3.9085 -0.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6826 -3.7666 1.0935 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1160 -1.4286 -0.8216 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3402 -1.3070 0.9761 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2373 -2.9681 -0.5149 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4693 -2.9522 1.2710 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5466 -1.6022 0.5347 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5337 -0.6340 -0.5594 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7374 0.3711 1.4140 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6390 -0.6377 2.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4343 2.9224 0.0133 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7155 1.7327 -1.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1341 1.8829 1.8292 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0788 2.4313 0.5222 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1922 -0.4024 0.9686 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2662 0.0012 -0.4848 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8977 -1.1557 1.0390 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3310 -0.1266 2.4394 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2060 1.8386 1.2373 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8220 0.6886 -0.1178 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0596 1.0854 1.3929 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0261 0.5435 2.8081 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2250 -1.5904 2.0174 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3331 -1.2886 0.3921 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7582 -1.7236 3.1067 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8466 -2.6883 1.6409 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4345 -0.0919 2.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9331 -1.7770 2.1622 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7297 -0.9044 0.1531 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4109 -2.0981 -0.1884 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2757 -0.3445 -1.7397 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8965 -0.1316 -0.6709 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1955 1.4496 0.7553 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7203 2.0957 -0.8384 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 2.6761 -0.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4047 0.9993 0.1838 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7609 2.1095 -2.6511 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1059 0.3448 -2.1988 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2235 1.1914 -1.2212 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8147 2.8203 -1.7322 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3765 1.8776 -3.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8807 2.5170 -4.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9989 0.2014 -4.4120 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4310 0.6941 -5.2667 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8047 -0.8387 -4.5291 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2468 -1.5856 -4.8051 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1882 -2.7970 -3.1782 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7612 -2.0601 -2.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2027 -0.7221 -0.8784 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2139 -2.4685 -0.8922 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4622 -2.5441 -1.7939 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3009 -1.4806 -0.4087 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4872 -0.3078 -3.2141 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8868 -0.6651 -2.2264 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0690 1.6739 -2.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5029 1.1194 -1.4669 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9491 1.9756 0.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4537 0.2902 0.5601 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8063 -0.3687 -0.4521 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1725 1.3648 -0.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3391 -0.0481 2.0806 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7956 1.6548 1.8626 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5803 -0.6909 1.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9868 1.0333 0.9700 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2489 -0.3858 3.6012 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7057 1.3331 3.4717 H 0 0 0 0 0 0 0 0 0 0 0 0 16.4918 -0.9934 2.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 16.6356 -0.0305 4.2451 H 0 0 0 0 0 0 0 0 0 0 0 0 17.1517 0.8548 1.3592 H 0 0 0 0 0 0 0 0 0 0 0 0 16.9665 2.0465 2.7499 H 0 0 0 0 0 0 0 0 0 0 0 0 18.2566 0.8286 2.7488 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 3 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 1 49 1 0 1 50 1 0 1 51 1 0 2 52 1 0 2 53 1 0 3 54 1 0 3 55 1 0 4 56 1 0 4 57 1 0 5 58 1 0 5 59 1 0 6 60 1 0 6 61 1 0 7 62 1 0 7 63 1 0 8 64 1 0 8 65 1 0 9 66 1 0 10 67 1 0 11 68 1 0 11 69 1 0 12 70 1 0 12 71 1 0 13 72 1 0 13 73 1 0 14 74 1 0 14 75 1 0 15 76 1 0 15 77 1 0 19 78 1 0 19 79 1 0 20 80 1 0 20 81 1 0 21 82 1 0 21 83 1 0 22 84 1 0 22 85 1 0 23 86 1 0 23 87 1 0 24 88 1 0 24 89 1 0 25 90 1 0 25 91 1 0 26 92 1 0 26 93 1 0 27 94 1 0 27 95 1 0 28 96 1 0 28 97 1 0 29 98 1 0 29 99 1 0 30100 1 0 30101 1 0 31102 1 0 31103 1 0 32104 1 0 32105 1 0 33106 1 0 33107 1 0 34108 1 0 34109 1 0 35110 1 0 35111 1 0 36112 1 0 36113 1 0 37114 1 0 37115 1 0 38116 1 0 38117 1 0 39118 1 0 39119 1 0 40120 1 0 40121 1 0 41122 1 0 41123 1 0 42124 1 0 42125 1 0 43126 1 0 43127 1 0 44128 1 0 44129 1 0 45130 1 0 45131 1 0 46132 1 0 46133 1 0 47134 1 0 47135 1 0 48136 1 0 48137 1 0 48138 1 0 M END

Standard InCHIKey	PIIMGTDCDZCLPE-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C46H90O2/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-33-35-37-39-41-43-45-48-46(47)44-42-40-38-36-34-32-16-14-12-10-8-6-4-2/h32,34H,3-31,33,35-45H2,1-2H3
SMILES	CCCCCCCCC=CCCCCCC(=O)OCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	674.69	Volume:	816.479 ? Van der Waals volume.
Dense:	0.826	LogP:	11.838 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	6.06 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-11.484 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	43.0	Rigid Bonds:	2.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.037	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.395	Fsp³:	0.935
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.663	Fluc inhibitor:	0.326 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.0 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.008 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.983	Promiscuous compounds:	0.312

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.122	MDCK Permeability:	-5.02
Pgp-inhibitor:	0.0	Pgp-substrate:	0.006
PAMPA:	0.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	105.422%	Volume Distribution (VD):	3.202
Fu:	0.043% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.019
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.999
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.234
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.66
CYP2D6-inhibitor:	0.968	CYP2D6-substrate:	0.99
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.837	CYP2C8-inhibitor:	1.0
HLM stability:	0.063 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

4.186

Half-life (T1/2):

6.12

ADMET: Toxicity

hERG Blockers:	0.974	hERG Blockers (10um):	0.988
Human Hepatotoxicity (H-HT):	0.257	Drug-induced Liver Injury (DILI):	0.004
AMES Toxicity:	0.003	Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.239	Skin Sensitization:	1.0
Carcinogencity:	0.07	Eye Corrosion:	0.998
Eye Irritation:	0.998	Respiratory Toxicity:	0.992
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.049
Hematotoxicity:	0.006	Drug-induced Nephrotoxicity:	0.097
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.997	Hek293 Cytotoxicity:	0.358
BCF:	-1.157 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.736 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.605 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.242 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16377847]
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2746	Apis cerana	Species	Apidae	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	Organism Name	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC491935 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	24737
0.1-0.2	22525
0.2-0.3	2103
0.3-0.4	343
0.4-0.5	86
0.5-0.6	43
0.6-0.7	10
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9032	High Similarity	NPC223677
0.9	High Similarity	NPC71761
0.8	Intermediate Similarity	NPC149299
0.7667	Intermediate Similarity	NPC80396
0.75	Intermediate Similarity	NPC128061
0.7097	Intermediate Similarity	NPC154642
0.7097	Intermediate Similarity	NPC80641
0.7097	Intermediate Similarity	NPC603612
0.7	Intermediate Similarity	NPC223249
0.6857	Remote Similarity	NPC28779
0.6774	Remote Similarity	NPC154396
0.6486	Remote Similarity	NPC277597
0.6471	Remote Similarity	NPC207815
0.6364	Remote Similarity	NPC309606
0.6316	Remote Similarity	NPC104537
0.6286	Remote Similarity	NPC163345
0.625	Remote Similarity	NPC286695
0.6	Remote Similarity	NPC475443
0.6	Remote Similarity	NPC473829
0.5946	Remote Similarity	NPC10316
0.5946	Remote Similarity	NPC200845
0.5938	Remote Similarity	NPC322892
0.5938	Remote Similarity	NPC12904
0.5938	Remote Similarity	NPC476550
0.5854	Remote Similarity	NPC330426
0.5854	Remote Similarity	NPC127091
0.5854	Remote Similarity	NPC22101
0.5833	Remote Similarity	NPC39633
0.5714	Remote Similarity	NPC54925
0.5625	Remote Similarity	NPC250028
0.5625	Remote Similarity	NPC236579
0.5625	Remote Similarity	NPC80234
0.5625	Remote Similarity	NPC86545
0.5625	Remote Similarity	NPC286498
0.5625	Remote Similarity	NPC223374
0.5625	Remote Similarity	NPC203531
0.5625	Remote Similarity	NPC196442
0.5625	Remote Similarity	NPC256163
0.5625	Remote Similarity	NPC301398
0.5625	Remote Similarity	NPC40597
0.5625	Remote Similarity	NPC608162
0.5625	Remote Similarity	NPC609004
0.561	Remote Similarity	NPC143857
0.561	Remote Similarity	NPC229252
0.5581	Remote Similarity	NPC48218
0.5581	Remote Similarity	NPC141481
0.5581	Remote Similarity	NPC464342
0.5556	Remote Similarity	NPC228473
0.5429	Remote Similarity	NPC310746
0.5429	Remote Similarity	NPC223675
0.5429	Remote Similarity	NPC68577
0.5385	Remote Similarity	NPC470237
0.5312	Remote Similarity	NPC40965
0.525	Remote Similarity	NPC148192
0.5238	Remote Similarity	NPC321919
0.5238	Remote Similarity	NPC476654
0.5238	Remote Similarity	NPC476655
0.5238	Remote Similarity	NPC476656
0.5217	Remote Similarity	NPC473559
0.5217	Remote Similarity	NPC324981
0.5143	Remote Similarity	NPC600941
0.5116	Remote Similarity	NPC271921

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC491935 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6907
0.1-0.2	2054
0.2-0.3	146
0.3-0.4	32
0.4-0.5	7
0.5-0.6	3
0.6-0.7	0
0.7-0.8	0
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
0.5641	Remote Similarity	NPD631	Phase 4
0.55	Remote Similarity	NPD630	Approved
0.5312	Remote Similarity	NPD900	Pre-clinical

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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